So a blanket policy that disqualifies everyone with a felony conviction doesn't make sense.

Probably something simple I am missing or the deal just doesn't make sense.3 condos, the owner has 14 out possible 48 in this complex and if the deal goes through may lead to more deals with her.the condos are 1/1, 2/1 and 2/2, she is asking 76k for the 2 2/1s and 64k for the one bedroom. total 216k, she would hold a second position note for 30k with me putting down the remainder of the 20% down (13,200) and pay closing costs. she would like 6 payments, one each year of 5200 for 6 years which comes out to 31200 total, about 1.5% interest rate if my calculations are correct.For simplicity, I am counting the 3 as a triplex, so rental income is 2325/month, tenants pay for electric and gas, HOA of 185(555) per pays for water, sewer and garbage as well as exterior and common area maintenance, snow removal, grass cutting, etc. taxes are 266 and insurance is 50 month (HO-6) policy which I hadn't heard of before.

Thanks for the suggestion.The house is on rural-ish island north of Seattle so it doesn't command the same rents that you would expect from Seattle.

This confuses me, I can tell from a basic layman way that something doesn't "look right" and should be repaired, but how do I know these costs professionally?

A simple umbrella policy often doesn't properly cover you, especially since many (if not all) of these policies have specific exclusions for cannabis. 

Doesn’t anyone see this as a good or bad offer ?

I certainly have learned just because there isn't a sign in the yard doesn't mean it isn't for sale.

They write their name or property address on the deposit slip and I can view the actual deposit slip.I also use Zelle which is instantly transferred to my bank account and is supported by all the major banks and is likely built into your banks app.I do not venmoe, it is slow and I have better 3rd parties.I also have some that use ACH transfers.All of these that I use are free to use.If they don't pay on their own then I give them a warning and if that doesn't work I start the eviction.I want rent to come in with no interaction from me.

HOA becomes insolventHOA doesn't put away enough money in reservesIf one entity buys more than 20% of the unitsIf the investor concentration exceeds 50% and there are other reasons but those are the ones we see most oftenIf it's non-warrantable, you've essentially bought into something, through no fault of your own, that you will have a difficult time reselling because it will be difficult to get financed. 

What @Ashish Acharya nailed as the issue is that the contribution of that property after the exchange into a disregarded LLC (one member - your tax return and doesn't file it's own tax return) is perfectly fine.