Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

Living in the property for two years likely allowed you to claim the capital gains exclusion... up to $250K for singles or $500K if married.

Your equity doesn’t matter in the taxes or decision.

Tax liens in MD are good for two years. 

You have the mortgage, taxes, insurance, maintenance, capital expenditures (roof, flooring, etc.), and also need to consider the cost of vacancies or bad tenants.I also recommend you charge market rate, for yourself and the tenant.

Chat with them, and ask them where they find their guest (Airbnb, Furnished Finders, Insurance claims, etc).

Instead, try reaching out to regional insurance adjusters or property claims departments directly.

Purchase price: $2,800,000 Cash invested: $560,000 The property is a three-story multi-family residential building with six independent units, initially facing significant challenges due to poor conditions.Renovation Investment Summary:- **Structural Repairs:** $250,000- **Kitchen Modernization:** $100,000- **Bathroom Updates:** $50,000- **Exterior Improvements:** $100,000- **Holding Costs:** $50,000- **Property Taxes:** $30,000- **Insurance Costs:** $10,000- **Management Services:** $10,000

Likely it is just a quit claim deed to your new name, however, also note that some states (ie MI - requires another form to be filled out and it changes our taxes - or can change them....).Get the help you need to make sure it is done right without costing you extra down the road.  

I guess it's just too many factors to consider and it easy to get overwhelmed and cannot get accurate info and estimation when I conduct analysis (ex. property tax rate, insurance, maintenance fee, rent, repair, closing cost, etc.)