But you can go to sleep at night knowing that even if you spend all you net income every month at least you are saving via 401k.

Can you sleep at night or do you have major hesitations when signing...these are all indicators that we are entering the high risk zone.

Regular homebuyers in your area might be buying a 300k house for 9,000 commission. 60k house you have to sell 5 for that 1.It  always amazes me that some investors think brokers or agents are an object to be used to meet their objectives.

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. 

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.

This happens every single day and night, and usually wakes me up from sleeping. 

So, you may want to form an entity for your first property so you are positioning yourself in a manner that not only protects your personal assets from the start, but will likely play a role in you sleeping juuust a little easier at night.Others did a great job commenting on this.

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. 

So things like personality, cleanliness, sleep/work habits will be right there with you when house hacking rooms.