If you take the individual investor model, you need to find a Whale.  

The idea is to convert a multi-family building into condos; but not in the traditional sense where you separate pre-existing apartments into their own condos; but in a way where you combine the common areas of all of the apartments in that whole building, and turn the individual rooms within those apartments into condos themselves; thus transforming the hallways, kitchens, bathrooms, living rooms, dining rooms, porches, balconies into common areas of the condos. 

You have a far better chance trying to sell to an individual than targeting hedge funds.

Most (not all) HELOCs require that the property is titled to an individual (not LLC) and are full doc, meaning your employment history, income, DTI etc will be factors.

I think that gets lost VERY quickly with certain individuals.

There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

Neither of us make over $150K per year as individuals members. 

Like I said before - if I, as an individual investor, can make the fee payment at once, how can RADD, as an entity with that type of professed liquidity, not refund the exact same amount - not more, not less - at once?

If a cash out refinance, many lenders will allow the cash out to satisfy the reserves requirement.DSCR lenders generally let you vest either individually or as an LLC.

Use caution when borrowing against your stock portfolio, especially if it's a high volatility portfolio comprised of individual companies.