You're going to pay taxes (regular income / short-term capital gains - both the same) no matter what.Double closings do have double closing fees, though some title companies won't charge a full double fee because, for example, they don't have to do the title work twice.If you're trying to prevent the seller from seeing what you're making, you can do a blind hud, or blind disclosure, or whatever it's called. 

They are great at verifying identity and address history.

I'm not sure if this is a good or bad idea, or if I should just stick with a regular tenant for my first rental, as I've got 3 other decent applicants. 

I am W-2 and I pay full mortgage for my regular live in house.

Instead of the weak public file we see, I got back about 10 pages of wants and warrants for failure to appear, failure to pay registration, false identities, etc.

It can be hard when candidates look identical on paper - here is a great article for you to read: https://www.inman.com/2019/03/18/find-the-best-tenant-and-maximize-the-roi-of-your-rental/.

This is much less costly than an Attorney to settle the issue once you are clear on what the rules state.Your HOA PM should be enforcing the current rules regularly and equally for all.

At the same time, 2 minutes' research shows that the regular cost is above $500, and that's the ballpark I heard from several attorneys I contacted. 

@Jeannette Tang A great way to house hack these days is to rent a 2-5 bedroom unit and Airbnb the rest of the rooms to other guests, the cash flow will be very high compared to a regular rental property, but it will not be comfortable doing it with a spouse because there is not a lot of privacy.

You may find they are behind on rent regularly or that they have unauthorized pets or people living with them.