The developments have continued to appreciate as I had hoped.7) I now have one last short sale condo under contract for $77k, which is a very low number around here. 2 bed/2 ba/detached garage, built 1980.

Also you have about $90k to invest.I see all those as advantages and not as obstacles. 

At 1200 sq. ft. and mostly original, this home has that old-school craftsman charm, but will need to have the 800 sq. ft. garage converted to a DADU (detached ADU) to have great cash flow.

Will need to have the 800 sq. ft. garage converted to a DADU (detached ADU) to have great cash flow.

One of the obstacles I have had to raising money from investors is that I have never been through a full cycle before.  

I bought my first house, SF detached, house hacked with roommates. 

They threatened to "detach" some commercial properties from Houston ISD and give the property taxes to smaller school districts.

I am running into some obstacles and hurdles when speaking to the larger banks for commercial property loan financing, seems like because I already have 2 properties under my name/credit its effecting my Debt to Income Ratio too high for their terms even though since I sold my business I have set aside a good amount of funds for a cash down payment so I am just trying to see how much the max I can be prequalified so I can start shopping around and making bids for different commercial property options. 

Prices have sky rocketed in the last few years, and the price of a detached home in Vancouver is approaching 700k (ouch)

A major obstacle standing in my way is the amount of student loans I will have to pay back.