Now we are in 2025 and although I still own the trucking company, it has been an inconsistent pit that has technically brought me personally no profit.

I have a good sized nest egg set aside for these things. 

Cash flow is definitely the biggest challenge; both in terms of finding properties to buy that cash flow with a loan on them and just company wide given interest rates and labor/material is up and, at least where I'm at in Jackson County, MO, taxes are way up too. 

Quote from @Dawn Harris: We have a STR managed by a property management company.

Presenting these insights to clients sets you apart from the competition.

You set your own payment terms with YOUR client and then find funding for them.The Capital Syndicate is a private lender firm that offers financing through their own company, but they also provide you with a list of about 150 other private lenders. 

I personally think they are a good company (that's why I hired them) but they may be too 'busy' for small fish like us.

If you have a solid team and some money set aside it's doable

Hey Adam,I’ve been in the Tampa real estate game for 20 years as an investor and owner of a property management company.

A cash-out refi could allow you to set aside some funds as a reserve or at least pay down your debts so that your lines of credit (credit cards etc) can act as your emergency reserve when more bad things happen.