We are legally bound to our contract in Orlando and have been for multiple years, thus a change in venues is not an option. 

The goal is to buy their home before loosing it back to the bank and in alot of cases we are able to buy and give them money to move onto the next stage of their life.

Condos have very strict rules regarding %owner vs % investment and can loose their condo cert if they don't abide.

You loose your capital gains exemption if you turn it into a rental (some exceptions). 

As much as 70% of the deals wholesalers bring to title, don't close, so you could very well loose your earnest money, as well as any expenses you put out for inspection, option money, contractor bids, survey, etc. 

Given how much you have, I expect you should have a heavy dose on those to keep a lower bound on your yearly income.

We also had an extra umbrella policy.Now that a few years have gone by and we've obtained more assets, meaning we have more to loose, it's made since to start an LLC and start to move things under its protection.Even if you get a good management company, which sounds hard to do, you'll still have to manage them and make sure they're staying on top of things.

If dogs are loose inside the unit and you are uncomfortable going in management will have to take that up with the renter And you will probably need to come back the next day to vet that unit.

There is just so much money to be made from this purchase and i don't want to drag my feet and let the opportunity slide by once someone else realizes the cashflow this place makes, and they buy and and i loose the opportunity.So i guess I'm looking for options for help with down payment.

Should I keep it or rent it out unfurnished (w/ management I will cut even or loose like $100 per month cash flow)?