Is the property under-rented?

Renting to farmers, tax incentives for farmers.

Did you sell or rent the home for them? 

I was planning to rent the room for around $800 and after I move out, rent the entire home out for $2,500 monthly.

The HOA restrictions limit me to renting the house only twice per year, and the insurance cost for rentals shorter than six months is significantly higher ($12K-$14K) compared to rentals longer than six months ($4K).

I recently bought a new home and rent my old home for cash flow of $400.

The biggest advice I can give you is to figure out your own goals, and be specific, so I want to invest in multi family for cash flow for instance is too broad, is your goal to have an investment or a place you enjoy living, those are often in conflict as most multi family tends not to be in the most desirable parts of towns, are you willing to high cash flow in exchange for alot more effort, risk and limited appreciation, or do you want a more stable property with potentially less or even zero cash flow, if it’s a primary residence, are you going to live there long enough to make it more sense than renting, the breakeven period in a place like Baltimore might be 3-5 years.

HI- I have seen the most success with a triplex or quadplex where you live in one unit and rent the others.

The Sub2 buyer would just pocket rent for a year or two, never pay the mortgage, house would get foreclosed on and original owner payed the price.#5. 

Make sure you thoroughly read the CC&R's because many also have restrictions on rental (% of owners that can rent, length of term, approval prior to,no short term, etc.).