That likely means that they are not good with money management which you are likely expecting from him.To answer your question, if you are doing long-term rentals, the LLC taxed as a partnership is likely the go to route.Best of luck.  

There is around 500k equity in the property. 150k-200k would get the property fully rented at top dollar with desirable tenants. 100k would get it to where I can rent all the units back out at fair reasonable market rents.

I previously owned rental property but sold them and am now looking to get back into real estate investing.

By purchasing a multi-unit property, living in one unit, and renting out the others, you can cover your mortgage payments and start building equity while gaining rental income.

I had a buddy with 5 SF rentals. 

Not all designers understand vacation rentals.

Can't beat the cash flow from a paid-off rental!

After 12 years in the furnished rental game, I'd say that is a pretty good sample size. 

While we currently live in Stephens City, VA, we’re open to investing in other states where the numbers make sense.Real Estate Goals & StrategyInvestment Focus: Buy-and-hold rentals, short-term rentals, and potential multifamily propertiesMarkets of Interest: Open to investing outside of Virginia in cash-flowing, landlord-friendly marketsCurrent Stage: Learning, networking, and preparing for our first investment propertyLong-Term Vision: Build a diversified rental portfolio that provides financial freedom and generational wealthWhy I’m HereNetworking: Connecting with experienced investors, agents, lenders, and property managersLearning: Gaining insights from those who’ve built successful portfoliosCollaborating: Open to partnerships, joint ventures, and creative financing strategiesWith my sales background, I understand the importance of negotiation, deal-making, and relationship-building—all of which I plan to leverage in real estate.

Begin by educating yourself through books like The House Hacking Strategy and podcasts like BiggerPockets, and join online communities for support.