I submit around 50 contracts a week with the official state contract (takes about an hour) and then work the contracts every week until the house sells.

They must pay the market rate, the same rate you officially list for the property.The good news is that you staying in your STR for the purpose of making repairs is not personal use.

As long as no “healthcare” services are provided (like medication or personal care), it’s not regulated by the Department of Health.

. 😊🙏🏼 I am concerned for your financial health:- I believe RE is more challenging than in recent times.- I believe the highest cash flow markets have the highest risk.- I fear a rushed purchase has additional risk.- make sure you have a good 1031 intermediary.- I believe the local market is challenging, especially with your goal of immediate cash flow, and not local (out of state) is higher risk and effort.Where is your current property that you are selling located?  

Here’s the play:Price: set a walk‑away number, then use an escalation with a cap tied to comps and in‑place rents; pair it with an appraisal‑gap limited to what you can comfortably cover.Terms: bigger EMD, short inspection period not waived, but prebook inspector and key specialists; ask for seller disclosures up front and use inspection to negotiate only for health/safety or structural.Lender: include DU/LP or pre‑underwrite letter, fund your reserves, and show shorter close with an ordered appraisal slot.Search: add adjacent submarkets with similar tenant bases where days‑on‑market are a touch longer; have your agent call the listing agent before writing to learn hot buttons and tailor.

It has not been well kept up, as the owner is getting old and has some health issues.

and they can usually just tell me if it will be worth writing it up and submitting an official written offer or not.

Employees (depending on your business model), property managers, contractors, the city/govt officials, tenants, partners (in the case of joint ventures).

He has some health issues; he said he wants to have cash on hand to deal with them in the upcoming years.

I'm officially a new Mortgage Loan Originator (MLO) and I'm now laser-focused on finding the right brokerage to affiliate with.