I figure if I start out with a low maintenance property, I can lower the learning curve and decrease the stress of managing a business and rental property myself to allow me time to figure things out as I go along. 

Walking back an agreement where you split the mortgage 50/50 and he pays utilities may be difficult and could stress the friendship. 

This will put you into your 50s.If you feel it will be a slow transition and you plane to concurrently carry your current source of income, that will eliminate you free time and add stress to the family dynamics and your health.In the next several years, the most crucial child development years in my opinion, you will not be there for your kids ...

The investing life before Jake was difficult, lonely, stressful, overwhelming at times.

It's going to drive you crazy and you've got bigger fish to fry... you're building your business and all the stress and energy you are pouring into this is taking away from that. 

It's so stressful and expensive. 

The fact that you are thinking about it may indicate the property is more stressful than it's worth.

Contracts don’t tell me anything more than that a clever attorney was hired to cross T’s and dot I’s. 

I do t have long term experience with them yet but They have a good track record and seem to really have it together from my experience.

I've managed a few renovations and it can be stressful and time consuming dealing with tradesmen and contractors.