I'm looking for a good real estate broker (preferably who invests as well or understands real estate investments) in the Jacksonville area that can help me find SFRs (or multifamily properties depending on the cap rate) for buy and hold.

For those kinds of properties I prefer working families that get settled in.

I only have roughly $9,000 to apply to the deal but would prefer to keep my out of pocket expenses as low as possible. 

You need the advice of a cross-border accountant - a professional that understands US and Canadian accounting and how they interact. 

To avoid investor competition, should I look more on HUD and Homepath properties since they give preference to owner occupants? 

I am looking for something between 20-50 units preferably, but nothing larger than 100 unit. 

However if they would prefer cash that's not an issue, just get a receipt from them to cover yourself if the IRS was to come knocking on your door. 

I think I would prefer to rent it out or borrow against the equity and continue living in it for now.  

There are plenty of listing brokers out there but would prefer to deal with a buyer's broker who has extensive experience dealing with investors and who is well dialed in to the local market and can be a potential source of new deals.

Thus, many investors prefer not to purchase properties with HOAs.Do a search on BP for HOA and you will find many discussions on the pros/cons.