It really does depend on timing of being put in service, that bonus it qualifies for (if any) and the life cycle of the elements that can be advanced. 

@Luisa Morejon Since you've lived in your home for 15 years, you qualify for a capital gains tax exclusion of up to $500K (married), allowing you to keep the proceeds tax-free.

BTW, it is illegal for a seller to receive any proceeds from the short sale,  however,  they may be qualified for relocation $$$ or other reimbursable expenses.   

I have also seen appraisers recognize that multiple ADUs by rule does not qualify for conventional F/f financing.  

I’d say if you did 2 or 3 smaller MF deals on your own and they went well, I’d say you are qualified to raise capital to buy properties similar to what you have already bought yourself.2 or 3 smaller MF deals does NOT qualify you to raise capital and buy 150 unit deal.I believe in step by step progress slowly and consistently working up the ladder towards bigger deals.

@Victor Yang To use the rental losses to offset any active income (W2), you'd have meet Real Estate Professional status (which would be difficult to do with a W2 job because you'd have to work more on real estate than any other job to qualify) OR have an AGI of $150K or less.

If you are looking at FHA because of credit score, then I would work on credit scores to qualify for conventional financing or see if you can get a very strong coborrower with high scores.  

They will have some questions and ultimately you can get pre qualified. 

I am grateful to you for sending me back to the white board. 

If you have $100k to invest skip over the cheap headache markets and go for a major metro class B or better part of city with high demand from qualified renters.