After spending £130 million in the summer on 12 new additions, Villa's value for money hasn't quite translated on the pitch after 21 opening Premier League games.
A long term injury to John McGinn and season ending blows to summer recruits Tom Heaton and Wesley have since forced Smith's hand in a notoriously difficult period to recruit top quality players.
Over the line
Danny Drinkwater has joined Villa on a loan deal until the end of the season. He returned to Chelsea after starting the season on loan at Burnley.
Drinkwater struggled for minutes in Lancashire, but through injury, the former Leicester man was out of Sean Dyche's favour from then on. The midfielder cost Chelsea £35 million after winning the Premier League with The Foxes in 2016.
After making over 70 appearances in the Premier League, Drinkwater has more top flight experience than any other Villa midfielder. For Smith and Villa, a naive backbone has been a major factor in a slow start to their Premier League return.
Only Jack Grealish, Tyrone Mings, Matt Targett and Tom Heaton have had a taste of the Premier League, which has clearly tested a young, fragile Villa squad up until January.
Last January, Villa's season also looked to have hit the rocks until successful recruitment altered their eventual fortunes. Mings was loaned in from Bournemouth with a point to prove last year, and now there's an opportunity for Drinkwater. After winning the league under Claudio Ranieri, Drinkwater's impact at Chelsea and Burnley has been minimal, but at 29 the midfielder is eager to get his career back on track.
Wesley's replacement
Searching far and wide, Dean Smith and Villa's chief scout Jesus Pitarch have scanned Europe and England for strikers after Wesley's season ending ACL injury.
Michy Batshuayi will not be joining Villa after early links to the Belgian surfaced. Chelsea teammate Olivier Giroud also looks unlikely to sign for Villa as the Premier League has ruled that only one loan deal is permitted from one club to another in the same window.
Whilst Smith haste ruled out the permanent capture of Giroud, his likely destination will be Milan, with Antonio Conte interested in linking back up with his former striker.
Elsewhere, Krzysztfof Piatek and Gregoire Defrel have both been linked to Villa in potential loan to buy deals.
According to Sky in Italy, Villa have tabled a £25 million offer for the Polish international who is now surplus to requirement after Milan re-signed Zlatan Ibrahimovic.
The goalkeeper situation
Tom Heaton's equally lengthy spell on the sidelines will be a huge loss for a Villa side so reliant on his leadership on and off the pitch.
Dean Smith has admitted the goalkeeper situation he now has to deal with is not a priority, but with only Orjan Nyland and Lovre Kalinic - both beforehand out of favour at Villa - available, Villa may pursue yet another loan deal to tie down a new number one in the coming weeks of the window.
Pepe Reina has been the only link to Villa over the course of the past week since the window opened. The 27 year old has covered Gianluigi Donnarumma this season at AC Milan.
Any other business
Villa have prioritised a striker, midfielder and goalkeeper as three positions to strengthen, but that doesn't rule out ant more moves elsewhere.
After all, Villa sit outside the bottom three by a point, and have so far play out a rather disappointing season, so recruitment in January is key.
Jarrod Bowen has been, for a long time admired by Villa, ironically the team Bowen's father supports. He has once more been in free scoring form in the Championship for Hull City. his goals have propelled them up the league, with two points separating them and the top six.
A back up striker is also on the cards, with the experienced Glenn Murray and the not so well known San Lorenzo striker Adolfo Gaich possible candidates to play as an understudy to Villa's potentially marquee January signing.
Looking to the future
What looks to be Villa's second piece of business this window will be the signing of 17 year old Louie Barry from Barcelona. The Birmingham born youngster signed for the Catalan club after coming through the youth ranks at West Bromwich Albion.
Villa's midland rivals, Albion, are however seeking legal action after Barcelona have not payed an agreed compensation fee when the England youngster joined the Spanish giants.