To not trust contractors even if family ( I was burned on multiple occasions).

@Corinna Gossner Any tax paying entity - corporation, partnership, trust, LLC or single or multiple tenants can do 1031 exchanges. 

Yes multiple

Being a general contractor and an experienced investor I see stuff from multiple angles and the key component of what you said was he is selling this property in the winter and that's exactly for a reason I've seen this happen many many times.

I'm basing that opinion on the fact that I've wholesaled a property that was on the MLS multiple times and didn't sell for a year.

Virtually wholesaling wise, that's hard to say since you are dealing with multiple state laws.

The biggest WHY is to hopefully have multiple streams of income through cash flow, in order to gain financial independence, to not have to work a 9 to 5.

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

I still get Tenants arguing that they can't pay rent until the second Wednesday of the month even though we discussed that multiple times prior to their applying and moving in.

We have a business plan, that includes a mission statement, basic guidelines/criteria and multiple exit strategies.