I'm not quite done yet and already have potential renters knocking on the door.

Forget boring; this is knock-your-socks-off exciting stuff!

It needs a new roof, a wall knocked down in the kitchen (to give it an open concept), paint inside and outside, new flooring and kitchen appliances.

The silver lining is that I hope to take this opportunity to remodel the home bringing the floor plan up to date, knocking out a wall, removing the wood paneling, relocating the water heater from a bedroom closet, etc.Here are few questions:I have read that some suggest getting a public insurance adjuster in order to get the most money back for repairs.

When I want to book it for months (instead of days) at a time, I just block it off for "owners' use" and list it in the MLS as a furnished rental.The only damage we've had (knock on wood) is a dent in the dishwasher panel.

In most cases, HOA's knock me way out of my price point. 

Yes but those are extreme examples and not the "norm" plus those come with very high payouts but very high risk as one would need to be extremely well capitalized, able to wait out for that one buyer (buyer's pool would be tiny at those price points).As an example of what I do successfully (most of the time anyway), I buy a 900-1500SF home in a very nice neighborhood in some of the hottest cities in my area, knock most of it down and rebuild a 2300-3500 SF home.

I’m not going to let this one blunder knock me down.

I'm thinking to buy a 2-3 bedroom condo/townhouse. Is it a good idea to live in own property and rent out other rooms?
In a situation when a roommate doesn't pay rent what are the leverage tools to force him to pay ...

I want our first house to be a house hack so we can knock out one of our biggest expenses.