Not sure if you have a place to live/call home, but by your content I'll assume you have a place to live and don't need to townhome yourself.

Also consider all lenders will require to review your insurance when underwriting a loan and it's likely a violation of your existing loan documents to let the properties go uninsured even if they didn't require insurance escrows. 

Maybe consider a conventional reno loan like the Homestyle or CHOICERenovation. 

Many Realtors will suggest purchasing a property using a FHA Loan, to reduce your out of pocket money.

FHA loans follow very strict guidelines when it comes to property condition.

Here’s the situation:Purchase Price: $540,000Down Payment: 20%Mortgage Rate: 7.125% (30-year fixed)Monthly Expenses (Mortgage, HOA, Taxes, Insurance): $3,706Realistic Max Rent: $3,000As you can see, I’m currently short $706/month even with max rent.

If they think your intent was to live in your home only 6 months, they may go after you. 

Look for loans such as DSCR (Debt Service Coverage Ratio) loans. 4.

Personally, I've bought older homes since I invest in mobile homes myself.

-Will it be robust enough to track additional business expenses that are NOT tied to a single property (IE; Business insurance, Home office, ETC?)