Because so many things can affect a sales price, the income capitalization approach (outlined in Sam's comment) is often the most reliable.

(I could not justify paying a $1/sq ft for painting when I can do it myself rather easily, it would have added several thousands of dollars to my cost)My long term goal is to do a cash out refinance in 24 months to pull out most of my capital and repeat the process. 

While the encroachment doesn't really affect my current intended use of the property I do worry about liability issues and what the next buyer could think.

What about if the inventory of houses available to fix and flip is super low would that affect how you rehab?

If you're in a growing, high-demand city, I'd love to hear how it's affected you.

I'm struggling to find out how this will affect my taxes - am I able to claim mortgage interest if I am on a loan but it's not my primary residence?

Anthony unfortunately you can evict someone just because they have a nasty personality unless it is affecting the neighbors or causing mold or some type of hazard environment. 

If you are selling the house the seasoning period won't affect you.

Did you mean that you don't expect the rate to raise before Aug, so it should not affect me?

Let me know if I'm forgetting something in my numbers below please: Buy purchase price $50,000 down payment of 20% $10,000 closing costs $2,000 total acquisition costs $12,000 initial mortgage payment $191 Rehab rehab costs $30,000 6 months holding costs $3,000 rehab costs + acquisition costs ($12k) $45,000 Refi house appraises for $125,000 cash out for 80% of that $100,000 cash out ($100k) minus total costs ($45k) and initial principle balance ($40k): $15,000 new mortgage principle balance: $100,000 new payment is: $477 Rent Market Rent $1,200 monthy profit (not including expenses other than debt service) $723 Repeat Investment Costs ($45k) plus cashout ($15k) $60,000 Annual rental profit $8,676Am I doing it right?