Quote from @Dan Farsht: I am looking to connect with other hard money lenders in the upper Midwest (our business is currently concentrated in the Greater Milwaukee Area). 

We rented the 2/1 side for $1300/mn and thought we could finish the addition of the bath and closet but got so busy with my construction business I still have not completed the work.

May negative cashflow until fixed.3) Buy established business: assuming you mean something other than real estate related.

I sold my precious business for 1.5M seller carry.

Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

The risk of "piercing the veil" applies more to LLCs when personal and business finances are not properly separated, not necessarily to individual landlords renting a portion of their home.A more practical approach is ensuring you have a solid lease agreement, sufficient liability insurance (including an umbrella policy), and properly reporting rental income and deductions on your tax return (Schedule E).

I navigate through cities and towns, identifying areas that are both friendly and challenging for STRs.

Is there a point of contact person/business that handles all home investor concerns (general contractor, engineer, etc.)

Hey, congrats on your business success!

I'm not thinking of 'scaling' my business by becoming a 'passive investor' in someone else's business.