The total property need a new roof, total rehab to the plumbing and the apartments that are not rented needs a total makeover.  

What is the overall condition of the building, roof etc?

Everything was replaced in the house with exception of the things that were new about 5 years ago including A/C, Plumbing, Electrical Service, and roof...

In general,newer is better.Unless you're talking about historical homes in special historical neighborhoods,a 70 year old home is gonna be worth more than the homes pushing 100 years that are probably long overdue for massive repairs and remodeling (new plumbing,rewire the electrics,new roof,water heaters,etc.

I wanted to make sure we're not missing anything before we close:Requested an estoppel agreement to be signed at the final walk-throughNew/updated lease will be signed honoring the previous termsRequested to see the rent rollWe have a copy of the leaseThe sellers agreed to replace the roof before we close; we asked for the roofers information to make sure they are licensed/will pull a permit, and to get information on the roof.Will confirm that security deposits will be transferredAnother concern/question I had is about paying cash for keys.  

Cashflow is negative, but Total ROI is 25-30%, meaning this would be an appreciation play and would provide a nice roof over my head and some gratification of owning a nice home.My guess is that it's somewhere in between these two scenarios.I'd still continue investing in future buy & hold deals, but this would mean I'd probably have to take a year off to rebuild my savings.  

Including roof or exterior, since obviously the HOA is not in control and has no capital reserve.My question is, how is this going to affect the future sale of the townhome?  

Roof begins tomorrow. 

I usually look at the age of the roof, hot water heater,  furnace, etc.

Iit's a double wide 2bdr, 2bth, New roof new carpet.