Yes very good job, absolutely no debt other than my rentals, I still live at home rent free and no car payments ect.

This sounds like an absolutely terrible idea, @Daniel Jost.

Purchase Price: $150,0003.5% down: $5,250Closing costs: $3,000Rehab (adding walls/closet for additional bedroom): $5,000monthly mortgage+tax+insurance (quote from lender): $1176 (1176*12= $14,112 for year)other monthly expenses: $300 (300*12= $3600 for year)All-in cash needed for year 1, assuming absolute worst case scenario and I can't find any single bedroom renters for the first year while I am living there:$30,962 After $7,500 room and board reimbursement from employer: $23,462I plan on pricing each bedroom way below market rent at $350/month, to try to fill up each bedroom and cut away at year 1 costs.If I can rent out 1 bedroom: (23,462-(350*12)) = $19,262 If I can rent out 2 bedrooms: (23,462-(700*12)) = $15,062If I can rent out all 3 bedrooms: (23,462-(1050*12)) = $10,862BP Calculator (after year 1) assuming worst case year 1 scenario:Note: I added money to "repair costs" to change numbers to reflect 12 months of mortgage payments I would have made during year 1.https://www.biggerpockets.com/analysis/rentals/df4b1eda-9cde-41ee-afb7-f8d9cdb8724c.pdfBP Calculator (after year 1) assuming mid-scenario where I manage to average 1 bedroom rented during the year I'm there.https://www.biggerpockets.com/analysis/rentals/df4b1eda-9cde-41ee-afb7-f8d9cdb8724c.pdfCoC ROI goes from 5.7 to 8.5.Also, I plan on eventually refinancing to a conventional loan, lowering my fixed costs from about 1200 to somewhere in the 800-900 range, freeing up 300-400 more in cash flow each month and increasing the CoC ROI.Would very much appreciate it if somebody could try to find holes in my plan.

I would absolutely look to turbotenant.com, hemlane.com or cozy.co they each offer similar services, but marketing, online rent collections, credit/background checks, maintenance work orders etc.

Ask specifically if they will count your rental income and what DTI they'll need to see to approve a new loan.Commercial lenders will absolutely require 20-25% down.

Those are condos and you are absolutely right, financing did become a problem.I don't know why the owner doesn't want to deconvert it first.

Essentially, he said they inspect absolutely everything and are very hard to work with.

I did buy 2 properties when I was there the second time in 2004/2005, and they've been great.I would absolutely start investing with a house hack. 

Smart, successful, absolutely.

Additionally, when private lenders are expecting a short term loan and that is not the case, it strains relationships I've worked so hard to build, through absolutely no fault of my own.