Are the strong businesses?

The free versions don't deal with any complexity at all.Unless you're a tax expert and understand all the intricacies of taxes related to rental properties I strongly recommend you find an EA or CPA who's experience with rentals.

If you have a strong historical capital and rent appreciation rate it might make sense to get into this market and wait for natural rent increases and appreciation to take hold and make for better investments if you wanted to stay local.You could also consider looking for turn-key investments in another city (Indy, Memphis, etc) where the returns could be much better - but the risk without having the ability to drive by the properties could be greater.

I also have long term business and friendship connections with them, so there is a strong level of trust.Thoughts?

Any advice or good practice to do in these cases other than a strong inspection contingency?

The house was built in 1990 and even though I have never upgraded the HVAC unit or water heater, they have been serviced and still going strong, no issues with this blizzard either.I will take my chances.

They will likely be signing.If one doesn't want to sign, best is ask the lender where they need to be to be relieved of the obligation and simply rely on one partner, I've seen both sign as partners and only one with a personal guarantee, when that one is strong enough.

Yes, totally understand the retirees aren't working but you'll still want a strong economy around them so that the community/town/city thrives.

If your eligible for financing now with a conventional their commitment should be enough for a hard money lender to accept that your exit strategy is strong...it would be expensive for sure however it would meet your goal of acquiring the property and covering the additional 10k your

If you would be staining it you would have to go with something less strong because the stripper can color the bare wood underneath and put some heavy dark spots in it.