I also self-manage my portfolio, but I also live here and have the time/knowledge/resources to do so. 

I am wondering if any lenders or knowledgeable investors know how feasible it could be to get a DSCR loan as a first-time home buyer/investor.

Mistake #3 was not having knowledgeable people around to be able to ask questions.

A knowledgeable attorney can advise here.Create a solid operating agreement: Since you own the condo with a friend, a clear operating agreement is essential to outline responsibilities, decision-making, and profit-sharing for the LLC.To save on costs:Look for real estate attorneys who specialize in investment properties and might offer package deals for the retitling, operating agreement, and filing the LLC.Shop around for title companies that can handle the transfer smoothly and provide competitive rates.Research DIY options for setting up the LLC if your situation is straightforward, though I’d still recommend a lawyer for the transfer process itself.Good luck with the process!

Especially now that consumer awareness and knowledge is at an all time high, expect the consumer to arrive at this same conclusion and ultimately demand this.

Work with a knowledgeable SDIRA custodian to ensure compliance with regulation.This post does not create a CPA-Client relationship.

Once you start to get people in there to look at project to project, that will give you a baseline then you'll start to gain more knowledge on where you need to be on the pricing/estimates etc.

He is a wealth of knowledge on the area and is actively investing locally as well.

It could be a nice opportunity however I would be certain they will want you to make up the difference between $250,000 and whatever is left on the mortgage which btw in my opinion should be done with lender's knowledge and approval. 

Happy to connect and knowledge share if you are interested.