---You can try to increase your chances of cashflow by buying a beatup property and BRRRing it.2) Buy Class C cautiously.

I have helped a lot of first time investors learn the process and successfully buy their first investment property. 

One of my CFO clients just did this last year and got cashed out over $1M, which he's using to buy more properties.

The Retainer Fee is credited towards whatever they buy from us in the 90 days, so in effect, costs them nothing.Note: we're not doing this to make money, but to avoid the time-wasters.

For a number of years I've formed transactional partnerships (form an LLC with single or multiple members to buy a building, build condos, townhomes etc).

Assuming the area checks out, I’d rather buy in a high price area that has little to no cash flow rather than an area that has cash flow but lower price.  

Our lot is fenced in and we cannot see where he lives but close enough to be of concern, but we want to stay in the same town until the kids are finished school.So, my question is this, would it make sense to rent our home (roughly $2300-2500/mo. as per real-estate agent claims), with the stipulation that the garage is used for my business AND buy a home nearby?

The hang up is getting deals formally drawn up.One idea:- I buy the property and pay 25% DP, then they provide capital after the closing and I pay them P&I over 5-10 years.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

He'll still be renting - just from you instead of others, and at all the costs to you that you have enumerated.Your son doesn't "need" to buy a house.