I think your best chance for success is to find someone who is in a unique situation and has to sell quickly or who is OK with leaving money on the table. 

Are the following issues pretty standard or are they unique to this company?

As I'm about to start medical school next fall, I've got a goal of developing passive income approximately equal to this salary so that I can eat and pay my mortgage on the condo (I plan to house hack again and live with another med student) preferably out of that rather than having to take out more loans that only have one repayment solution. 

Agreed to what Cody stated above and each deal is unique to local conditions. 

Some have had HELOC's large enough to buy the property with the HELOC, renovate it with the HELOC, followed by a cash out refinance on a conventional loan to repay the HELOC.

I'm finding off-market houses that are on larger than average lots, where a lot or two can be split off and sold.  Whether the original house is kept as a rental or fixed and flipped, what ROI are private investors lo...

Instead of paying for them by the income approach   Its kind of a unique area. 

Rolling funds can offer unique benefits to LPs, founders, and GPs.LPsFor LPs, rolling funds offer an easy way to diversify and invest in startups.

As it is "they" are now realizing that tenants are not going to be able to repay the rent -  so soon they will want us to just eat it...... 

I know there will be even more fees if I close this line of credit out early (within the first one or two years) but I'd like to move on and write off the extra expenses (closing costs/early repayment fees) as a learning experience.