I am interested in purchasing tax liens and properties at deeds sales to create a STR and LTR portfolio.Would love to connect!

I expect you will have to pay transfer taxes based on the assessed value of the condo unit in order to transfer the deed at this juncture. 

For a 1000 unit SFR portfolio in Tampa, you could have a portfolio manager in Cleveland, OH, a call in Center in Topeka, Kansas, remote customer service team members in Mexico or (offshore) in India, and a rental payment processing center in New York.

An Option that is closer to you and affordable is Vegas.. some of the lowest prop tax's in the country no big weather extremes find newer homes and ready rental pool.. with mid term rentals a reality. 

But if  you break it all down yourself, its a negative CoC return and you are losing $......yes there are tax benefits, loan paydown, etc. but that still doesn't make up for the fact you are profiting 0, especially if you are investing in a cash flow marketIn the end, if you are just looking for places to park $$$ for the long term it may work out, but if you are looking to make an annual return on the money you put in there may be better ways of doing it.Just my 2cents on this, I'm not a big time investor like some of these guys and they are a successful for a reason.

However, in my market a nice unit can easily collect $120,000+ in rent (not taxes, fees, or other pass through costs) and when the locals demand 35% commission my 20% is a steal and isn’t a whole lot more work for the 25k+ a year I’m making per property.

And another $200 in property tax.

The added benefit is the equity you have now created in your personal residence that can avoid capital gains taxes if you live there for at least two years. 

Is he required to issue me a 1099 form for rental income for 2023 taxes?

I am wondering if I can save some money and just do the tax myself by using TurboTax Business, especially because it's the first year of LLC with only a couple of expense items?