This effectively means that I don't need a primary residence at least for the next few years and my living expenses are practically 0.

We currently have 1 paid off home in woodland park that we have been renting for the last 4 years and wanting to grow .

Rather than taking out some boot from your sale to pay off debt, you could take a detailed look at your financing math after buying a new property and then strategically refinance to replace expensive debt with cheaper debt, but this is not very easy in today's rate environment. 

In both cases I spend a lot of money rehabbing a house and then pay myself back either through a sale or refinance of the property.Up to this point, I have primarily just paid for everything through my business checking account.

That being said being so quick to grab na property at my young age it may not have been the best deal; but I put 0 money down and actually got paid to purchase this property so I guess I didn't do too bad.

The perfect way to have a vacation home that is paid for by guests!

Use 50% rule, expenses are $1.5k/month.  

If an insurance company is replacing roofs every 5-10 years they will go out of business unless insurance was much much much more expensive.

Land cannot be depreciated but the building, land scaping and other capital expenses can be. 4.

Rates: 9% to 13% (Most Deals are 11-12%)Terms: up to 36 Months (Most Deals are 6-12 months)Fees: 2-4 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 (For loans less than $250,000 $2,500 minimum fee)Max Loan: 65%-70% of After Repair Value(ARV)100% Rehab Financing Available (Require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 2 Weeks)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.