Not only did it help us out financially, but it set a great example for our kids who saw us working hard and doing it ourselves.

Its  courageous step and seems like you secure yourself financially before  jump in as full time Investors.  

I'm very reluctant to give in, its nice knowing if for whatever reason we can't re-rent, the current tenant has to meet their contractual rent obligations. 

Age is not the right question to be asking in my opinion, knowledge, financial stability, and comfort level with a given strategy are far more important.I would love to get your thoughts on this and read your article when you're done.

In that case, certainly get the seller to sort that out first or you could have a headache.The property management company that I like and trust never hold you to such obligations from the start, they operate with the highest quality of service and basically maintain that if you don't like them you don't need to work with them.

In regards to over-leveraged and being vulnerable, you need to decide on your own financial situation. 

Found 3 on the market, got the rent rolls and financial statements(if you can call what they gave me that).

You can find a lot of good information at sense financial.

Option 1: One mortgage, both on it, you're coborrowers, no different in terms of responsibility/obligations/etc than an engaged couple buying together.Option 2: One mortgage, only one person on it, the other person can be property manager or whatever you work out once you own it.Option 3: One person on mortgage, both on title.

I am unsure currently of our friends financial situation as far as him putting any money into the deal himself.