I manage around 400 rentals with 14 years of experience and have never been sued once.

After 6 months I have two properties and since day 1 they have been rented.However, making some numbers and organizing the 2025 budget I am not sure what to think about my first step on this journey.The rent covers the mortgages (10 year loan both) however I have to take out of my pocket some % to cover HOA and management fee.

It would just need to be a situation where they have great contact with the person doing that managing of the project (I.e. have known the person for years, great reputation, person has experience in flipping etc.).

@Jason Brown - I'm a CT based investor, flipper, and property management company owner.  

Try interviewing at least three managers.1.

It’s definitely worth exploring if you’re looking for a robust management tool.

He get's principal and simple interest payments over a number of years.I'll manage the deal and the property.Looking to create a proforma for this that would fit a typical rental analysis but insert the detail of having private money cover the DP.

I'm now figuring out how to maximize the return on current properties and add value, efficient ways to self manage, etc.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

I work with Property Management in Houston but can recommend some great networking/educational events for you :) Check out Space City REI - there's monthly meetups with an educational speaker relating to real estate investing and there are plenty of Investors looking for Wholesalers out there!