I own a 4plex there and I have one unit that has been vacant for about 4 months now and this seems on the high side of vacancy time.

Today it is more than 10 times that.

I own a unit at a local condominium complex and am having issues with timely response from the HOA. 

A lot of investors are jumping to secondary lines of insurance coverage and the problem with those is that the companies are based in the Cayman Islands or the Bahamas a lot of the time, and it is suspect that they would actually pay out if the need arose unfortunately.   

I would suggest finishing school, working as a part time agent while you are at school, saving commissions for investing, and working with a team that focuses on investing as opposed to residential sales.There are also local meet ups every month. 

He'll have at least $2k per month in positive cash flow and tons of equity when it's time to find the next home in some years.

@Ella Marie, I can't speak on behalf of your market, but in my respective market, competition is tough, and the successful fix-and-flip vendors are often full-time operating businesses.

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment. 

Unfortunately, over the 11 months he has lived there, he has only managed to pay the rent on time once.

(Available time, money, income, family situation, credit availability, time horizon, real estate market location and phase, medical situation, etc etc.)