Recently, through my church network, I had a brief conversation with the CEO of a real estate investment company specializing in auctions.

Structuring the deal properly (like through a land trust) can reduce this risk.Your best bet is to connect with an Illinois investor who has successfully done sub-to deals or find a local real estate attorney who specializes in creative finance.

You should be fine, and I doubt anyone will care or say anything specially in a DSCR loan.

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

Here’s a quick overview of potential pros and cons, along with general advice on working with hard money lenders like them.Pros:Flexible Financing Options: Rehab Financial Group often specializes in real estate investing and provides hard money loans for BRRRR deals, which may be a good match for your needs.Quick Funding: Hard money lenders like Rehab Financial can sometimes offer quicker access to funds compared to traditional banks, which is important for BRRRR investors looking to move fast on properties.Cons:Higher Interest Rates: Hard money lenders usually charge higher interest rates than traditional financing sources.

(ii) Can anyone recommend an agent in the Philadelphia area who specializes in apartment buildings? 

I specialize in investment properties as a real estate agent, and I’d love to connect and help out where I can.

Hi Itay, I'm a vacation rental designer that specializes in data-driven design to maximize ROI.

If you’re feeling uneasy about the potential headaches, you might consider a local property manager who specializes in room rentals or shared housing.

All good reading and listening, education is best and if you want to learn you have to ingest as much information as possible.I read many books that helped me, but my go-to is listeining to at least 2hrs of podcast with real examples per day.One very important things that "want-to-be" fails is to understand that real estate has many different specialities, so you have to focus your time in your real project.