They may shape up for a bit while they figure out who you are but they are likely to get right back in the red and it may come quicker than you think.If they are not 100% by the time you close, I would collect their first month's rent (make sure it's good) and then serve them notice to vacate.It's common for new Landlords to say, "I don't care if they're bad tenants because I'm getting such a good deal!"

@Jeff QuinlanI don't see much of a big deal with requesting the tax return or the part of the tax return that shows the rental portion.Seeing the numbers on the return shouldn't provide you any further re-assurance.You should do your own due-diligence.The seller may not have many any repairs/improvements and in which case the building may be in bad shape and you, the buyer, would have larger expenses going forward.The figures on the tax return may be inflated/deflated.etc.

Keep in mind that CT law requires security deposits to be kept separate from operating expenses, so those are in no shape or form hastening your return of capital.

I am sensing a trend here... that is most do it on their own/small until they have the balance sheet to be their own guarantor for fannie/freddie

This is what you would do for any rental investment.For condos, there are at least 2 additional things I can think of to keep in mind: trend for HOA fees and capex reserves. 

My realtor suggested this language to stave off the trend he has seen of people asking for more work to be done on already remodeled houses.

A house that looks like it is market ready - 10k rehab; a house the needs an update, less than 2000sqft, 20k-30k and add 10k more if the house is larger than 2000 sqft; any house that is in bad shape - start at 50k rehab and add 10k every 500 sqft above 1500 sqft; high end homes have rehabs that are more expensive and need to factor the area in, to get an average house in a higher end neighborhood to go from 300k to 500k can take between 50k and 80k even up to 100k, higher end finishes are much more expensive.So I will try to have a rehab estimate in my head before I go to the house.

Very few come on the market, and the ones that due are usually in terrible shape or so overpriced that they don't come close to cash flowing.We owned a duplex on Live Oak near Skillman, bought it in 2013, we bought it and there were multiple offers, and we sold it in 2016 for a really nice gain with multiple offers. 

Place is under 300k total, not the best shape but manageable.

I do think that the smaller cottage home trend will.