This site is a gold mine of knowledge, some of the experts that chime in regularly have many decades of Real Estate Investment experience and happily help new people. 

Even if you find the right deal, securing the right type of funding can be a pain.

Some loans are secured, while others are not.

So you should be aware of that and act accordingly, by making sure you have a way to check on the status of the loan payments regularly.

The HELOC is secured by your personal house, the new loan likely the property.  

Her advice, candor, helpfulness, and willingness to do what it took to secure me the best possible outcome was incredible.

If you have handled everything correctly, being strong when needed to be, and doing evictions when needed, the Tenant will feel secure because the Tenant will know what is expected of them and will feel comfortable and will want to stay.

That said, I'd like to raise the rent by $25-$50 per month and put them on a 12 month lease with the condition that if they found their home, they can move out once we find a replacement tenant (and we would focus on securing a new tenant ASAP).  

Don’t allow tenants to move into the property unless they have rent and security deposits PAID IN FULL!!

Historically the 3 markets Matt quotes regularly (San Fran, LA, and San Diego) have a great historical rate of appreciation going back many years (at least 60 year in San Diego).