The average time to flip a home is 6 months --again averages, but with a solid network and referral partner you can find incredible deals that are far less price than $250k (like $70 - $90k) and average profit potentials over double from the 20% average example, pending on extra hands provided for your daily research.

We don't want to sell the house but want to make sure we are covered as much as possible on the extra liability of renting a house with a pool.

Accounting function is extra so I don't know how that looks.If you are just starting, it might worth using it since it already comes with the BP Pro. 

I want guaranteed monthly rents because when I purchase my main focus is cash flow, then equity in the form of added value (renovations, adding extra bedroom, etc).

For example you finish the attic and add a 3rd bedroom or you take the already there illegal attic or basement unit which are common in Chicago and connect it to the legal unit for extra living space so now you have 3/2 duplex rents on what used to be a 2/1 simplex.

It's easy to obtain, costs very little, and doesn't require extra, on-going effort to maintain.

Yep, I used my HELOC to help me pay cash for my first two rentals. 3 years later I did a cash out refi on one of them and got all my cash back plus an extra 10k.

I always thought he went the extra mile to save me money and he knew what looked the best.

My realtor suggested about 10k-20k extra in value.  

If your property is a good mid-term candidate, then it's just a matter of whether the extra effort is worth the extra income to you.