I'd hate to be tying the knot on a great deal and have my lack of knowledge on my own contract destroy any rapport I have with the seller, and lose the deal. 

They destroyed my house, I had to evict them.

It's not a full remodel, just paint, floors, and maybe AC, so I wont be doing projects for the rest of my life. 

Im only 20 years old I feel like i wont be taken seriously as a "cash buyer", and thinking of being bombarded with questions i may have no answer to is holding me back.

once the market crests, which it may do at any point, then there wont be many good properties on the market, and we will only be left with the junk which has poor tenants, or is in bad shape and the owners have to sell. 

We have a liquid enough market though that we can disclose that the house is falling down and someone will still buy it anyways, and in DC proper most people dont even do inspections because the market wont allow it.

The threshold is not coming out without being destroyed. 

depends on the company some might.. some for sure wont..

If you make the deposit non refunadable they wont care and figure they already paid for damages so will not take as much care. 

conventional financing wont work without income. so your in great shape.. find owner deals.