They'll likely have follow up questions about who handles maintenance, larger SD, etc... so be prepared to quickly answer these.Value to mention:- Professionally cleaned property after each stay and exterior upkeep- Staged photos that you can share with the owner for marketing purposes- Capex coverage up to $XX,000 (might need to include in SD)- Extra $XXX per month (likely may need to pay a little extra in rent to make it worthwhile, otherwise they can collect the same amount as LTR)Also, google "Airbnb apartments" or check their website. 

If you can tolerate it, go for the extra roommate.

- Rent out the extra bedrooms in your unit to roommates or for even higher rent on Furnished Finder.- Rent out the other unit as STR or MTR for max cashflow - which will require you to become an expert at those businesses.- Learn how to do your own repairs & rehabs to save money now.

I'm soon closing on a multi-family property that has some extra space that's begging to find a better use. 

Just having an extra kitchen doesn't impact insurance eligibility. 

No extra fees added for repairs, I'm allowed to contract my own people via the PM to do services(HVAC, lawn, water heater, etc.)

You’ll need to find a GC on board with the extra paperwork and a seller willing to accept a longer closing time.   

My opinion-- buy in the winter, underwrite with an extra long vacancy, get some seller concessions to defeat the cash flow if it's really that tight.

I would have an extra light on a stand to brighten the spaces.2) Your first photo is of an empty room to a doorway.

The least risk would be to use the extra 100k a year to buy bonds and then sell the bonds to pay the mortgage each month.