I really hope other new investors take the time to read what you shared.

The 1st crawl space company came in and said they are not concerned at all and would recommend fixing the floor from the interior. 

None of the concerns that you have will matter, as income, your tax returns, or net figures don’t affect the loan at all.

So sustained maintenance should not be your concern, your concern should be on how fast you can recover the initial cost of the hot tub, the maintenance is not the issue.Argument #2 Seems like this is based out of fear and the unknown.  

My biggest concern is: I would like to have this property cash flow $200 monthly and I'm not sure if the market would be able to support that high amount of rent.

Most lenders are just concerned with PITI and HOA when they qualify your dscr, but you will want to make sure you account for management if you are choosing to use that service so you know how much the property will make. 

Moisture damage below the sink and in a bathroom ceiling which is slightly concerning.

Usually, self employed hide money by not taking a "salary" but taking a "draw" / profit share.  

but there lies my biggest concern, while I am investing in areas that I believe are going to appreciate dramatically as that is where some real money is to be made, I am buying to cash flow and not guaranteeing to myself or to anyone that the appreciation will really happen.

Are you concerned about theft allegations?