Stan, your heart is pointed in the right direction but resistance is futile, as they say.

I'm a worrier by heart.  I

In that case my simple, hearty exhortation is:BUY BUY BUY!

i just had a townhouse opened up because a tenant that couldn't afford it had to move out. it really does suck to let a good tenant go, and seeing her just falling into this economy broke my heart. i gave her a grant, helped her move, and also offered her my garage for storage in the meantime while she's with family now. i really want to avoid this happening again. and i was wondering what are the measurements that people take now adays to make sure you're finding a tenant that does have a good job and good intentions. i'm terrified to see another tenant breaking in front of me like that. also i have a friend that told me that he found a tenant, signed a lease, and a day later he was already making problems and he's not paying rent. he was totally scammed and now with no evictions - he basically have someone living in his house for who knows how long. these are scary times for landlords, and i really need some good advise what to do and how to approach the next potential tenant. thank you all!

If your heart is set on college have you  thought about joining the military and doing a short tour?

Most people collected a hearty option fee for the restriction that option places upon the landlord during the option period.  

If your heart is set on a small multifamily house hack, research Fort Worth.

I have let my diet slip into junk food, alcohol, and constant grazing.

It is like going to the gym everyday but not managing your diet.  

Make believe you just happen to have something you think he will like e.g. some really nice chocolates or a good wine and tell him you need someone to give it to because you are on a diet.