Looks like a young group of professionals with not enough experience, navigating through various market cycles to produce an accurate  business case.  

No, more specifically deals found through networking with local real estate professionals, finding pocket listings, direct mail, etc.

Networking with real estate professionals is huge, too – it opens up so many opportunities.Would you recommend starting with fix-and-flip projects or something else for someone new to private lending?

Not that that means anything good or bad :-) But if you want high quality genuine coaching about investing in Philly and at a reasonable rate, I can  connect you with a wonderfully savvy, professional investor who does coaching.

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

Review your loan agreement for restrictions, and consult legal and tax professionals to ensure compliance and protect your interests.In C State, you can elect to file MMLLC as disregarded entity for tax reasons.

Professional roommates?”

Exceptionally knowledgeable, very professional, and service oriented.

Unless you are a seasoned real estate investor with professional title searching skills, I wouldn't do this.

Speaking from past experiences vetting the real estate professionals that you chose is paramount.