Difficult for partnerships, requires good relationship. 

The difficult part will be finding the 1. 

I am starting a new STR business and I have been trying to look for property here in the Orlando and Kissimmee area but its been very difficult.

It's slightly difficult to navigate, but I think it's because we're trying to comprehend the real estate world.

I want to add some rentals to my small portfolio but have been finding it difficult to find anything to buy.  

One last thing its difficult to get any information on existing wells because most were done by home owners or the companies didn't record anything with the city.

My friend and I are trying to get our real estate careers started, and we're finding it pretty difficult to afford the 20%-25% down payments for the properties in our area.

As a complete beginner, I would appreciate feedback from the community on things to consider when looking at this particular geographical area and when purchasing a multi-family home in the next 6 months in today's difficult and expensive market and yet still come ahead by lowering significantly the mortgage payments or even breaking even.

If you're in a small town, it may be difficult.

On second home loans you only have to put 10% down, I would just do that if I were you, sounds likes a great opportunity (also you maybe surprised  doing seller carry on 20% is not nearly as difficult for the seller)