something that seems to surprise new investors is that transacting real estate is expensive.in Pittsburgh transfer taxes are 5%, usually split between buyer and seller. 

If you are considering renting it for a minimum of 30 days, I believe you will be exempt from any short term rental rules and taxes. 

Start by clearly outlining your renovation goals, and follow up with an in-person or virtual consultation to ensure both you and the contractor understand the vision for the project and expectations.

A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.

But I also love the idea of investing in real-estate and utilizing its tax benefits I have read around 10 ish books or so and the one I am reading right now recommended this site I am looking for some advice of things I can do to either prep for an investment into real estate and or do right now.

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

So, instead of paying taxes on $50K, I'm paying taxes on only $21K. 

Have you never filed taxes before?

This should include potential rental income, expenses (including property taxes, insurance, maintenance, and potential vacancy), and your expected return on investment. 

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end?