My wife and I will be paying taxes on the gain from the condo but will he have to pay any gain and do we have to hire a 1031 company since nothing will be held in escrow? 

Let them set a month to month lease and then pay you as the cleaner/maid/contact person.

Rent: $450Deposit: $450Tenant pays own electricI pay water* I need to put $1,000 worth of work in it to get it ready to rent

In order to get the highest CMHA rent possible, your unit will also have to be fully rehabbed, you will need to provide all appliances, and pay all the utilities. 

If you own a property outright and get sued that property can be foreclosed on to pay that judgement debt, but if it is fully leveraged with a loan it isn't worth them trying to foreclose on because there isn't enough equity to make it worth the effort and expense. 3.

I had sold a dump truck back hoe trailer on contract.. guy would not pay me. 

So, if I did do it that way I would need to pay gift tax on the money he gave me for the rehab, correct?

You don’t pay any capital gain taxes.  

For all of you W2 guys and gals out there if you lose your job- try to get a new job as soon as possible that pays as much as the old one.

I'm a put your paycheck in the bank guy, not a collect rent, cover the overhead, and pay the taxes type of guy.