City planning had lots of insight and a 'bigger picture'.

The next option I thought of was buying a rental property with money I have saved up, renting that property and using its cash flow to cover the rest of my dads mortgage.

Soft costs will vary based on impact fees, professional fees, RE taxes, carry costs and mistakes covered in your contingency.

Carrying cost is high; for 4 extra months would cost me almost $10K if I stick with the HML until 6 month seasoning is covered.  

I think there is a lot of great resources out there and the class itself covers everything you need to know so if I did it again I would do the cheaper package.

The payments coming in from the installment sales contract cover the payments on the monetization loan.

I cut and pasted this from the Massachusetts Housing and If I were you I'd check it over. (3) Property Covered By M.G.L. c 151B, s. 4.

My hope on this specific condex was that I could rent the first unit (questionable if it is "liveable" though it is owner occupied now - he's in preforeclosure) to cover the mortgage, while fixing the back unit.

Never use the safety deposit to cover repair costs when the tenant is still in the unit. 

My sister and her husband will be moving to Austin for his job next year, and thanks to my constant chatter about BiggerPockets and real estate investing, they're interested in house hacking by buying a small multi-family and renting out the other unit(s) to cover their living expenses.They aren't on BP, so I'd like to help connect them with a few competent, investor-friendly real estate agents in Austin who have some multi-family experience.