Looking to jump into to STR in Florida, considering paying all cash

[Ben Kelleher]

Recently, we did quite well on a business deal and found ourselves with quite a bit of cash to invest, particularly in real estate. We have chosen to target 5-6 bedroom homes in Kissimmee, FL due to the excellent short term rental market. Our plan is to buy the first home in cash, likely $550k-$650k, operate it under management for 3-6 months, then refi to pull out what we feel the property can support for a mortgage so we do not end up upside down. Then we will put the cash from the refi towards another property with even less capital investment than the first property, etc. Are there any major flaws with this plan, other than tying up a significant amount of capital on the first property? I see a tremendous advantage to getting deals by buying with cash now since we have it, as well as making sure we do not end up underwater on a mortgage due to unforseen expenses as we are new to the STR game. Please take a minute and shoot some holes in this plan, if there are any. I'd like to go into this as educated as possible. Thanks!