I purchased for $420k and the house needed quite a bit of updating/fixing and furniture, so I spent another $64,000 in repairs using my savings along with credit cards...yeah...ouch...I know...  

I talked to 6 people this week who went out of state for more cash flow and are dealing with negative cash flow now (properties looked good on paper but maintenance, repairs, capex, tenant and PM issues have caused significant losses for them in reality).

Regarding your query regarding getting a loan to repair a multifamily property, you're on the correct road by producing a business plan.

The downside is more maintenance and repairs, more toilets, stoves, water heaters etc...Depending on what your goals are for the investments and your acquisition strategy would point you toward one asset class or another. 

If you are looking for control of your property to maximize returns, you will need to manage it yourself and confirm with the existing HOA what you can and cannot do (and what services your guests can and cannot access if you manage it). 

Something else to consider would be that you already likely have cleaners, handyman services and the like in Orlando area.

Servicing existing residents and leases upon purchase.

They changed their mind real fast when they realized they not only had to pay to repair their property but also mine and the other neighboring property.

Our long term goal is to establish our business over the next couple years (generating income history, credit, credibility, etc.) before I retire from military service and transition to full time real estate investing. 

I thought I’d have to use a service like LegalZoom because they have so many options on their site.