To heat a large 3br apartment, electric heat would be really expensive, and those ductless wall systems I hear require a lot of upkeep/maintenance which I can't depend on tenants to do and would prefer not to have to be there once a month to maintain myself. 

This tenant is great and I like maintaining a good rapport.

I would like to maintain the property, but also ensure costs are low for lawn care. 

Use Zillow and search specifically using Foreclosure or Pre-Foreclosure, actually drive the neighborhoods and look for homes that appear to be vacant/have overgrown grass, homes that look Leila they haven’t been maintained.

Over the couple years of living in the property I remodeled both bathrooms, replaced the roof, and properly maintained the home.

Seller maintains income.

My concern with rental properties is the amount of work needed to maintain it (tenants, finding property manager, contractors, late rent, eviction, tax papers, finding more properties ).

.* The homeowner must cooperate with the real estate agent's efforts to sell the home and maintain the interior and exterior of the home.* The servicer and homeowner must meet a number of time frames.* The homeowner cannot have a close business or personal relationship with the real estate agent or buyer and cannot have an expectation of buying back or renting the home after the short sale or DIL closes.* The lender may require the homeowner to make full or partial payments on the mortgage, up to 31% of the homeowner's income, subject to the lender's written policies.* The lender can initiate or continue, but not complete a foreclosure sale while the homeowner is involved in the program.* The buyer in a short sale can't resell the home within 90days of the purchase.There you have it.

I’m only buying in indy since I manage and maintain my properties. 

If I were to sell a property on land contract, how do I ensure that that the buyer maintains homeowner's insurance and stays current with property taxes?