Our goals at this time is to diversify our current investments with real estate and possibly build to a point where it could replace my wife’s income so she may have the option to retire early.

In the short run it's ok to lose $10,000 to save yourself ~$1mil if you think about it.

Cut back and save some $.

But I've lived through the success of local real estate investing, careful saving, and investing in SFR and small multifamily.

I just found out that our maintenance guy who we've had handle most common requests on our commercial properties is retiring and I've been searching to find a replacement.

It gives you also access to a lot of fringe benefits and open the door to many retirement plans options. 

Saves me pulling out 30K PLUS closing costs and then holding some 6.5% RE mortgage rate to deal with.I'm not sure how to go about this or how to present it to him. 

Tyler, save up a down payment and buy your own house and rent it out whether it’s long term or short term. 

Right now we take cash flow from rentals and save to buy next rental property with cash.

I have a good friend who recently retired from active duty, and is preparing to relocate to another state.