I do like your buy & hold strategy, but unless you really enjoy driving to tenants to collect rent every week, you should consider requiring your tenants to sign up for automatic withdrawal from a checking or savings account.Collecting rents in cash creates the opportunity for payment disputes, not to mention being a security risk and a huge inconvenience for you.If you're goal is to build a serious portfolio of properties, you'll need to resolve the rent payment issue sooner or later.

If I raise the rent to $575 will Sec 8 automatically pick up the rent increase since the portion the tenants are paying would be considered the 'most' they can pay each month?

If it's stated in your lease that this is what happens automatically, you already have it in writing.

He filed for bankruptcy right before appearing in the eviction court and the eviction case is on an automatic stay.The tenant is still living in the apartment and not picking our calls as we tried to work out. 

At this point, I'm pretty excited because I now have a computer program that not only automatically gathers data on distressed properties, updates monthly (automatically), but it also gives me the mailing info I need and formatted correctly to be sent directly to the printer I use for mailings. 

At this point, I'm pretty excited because I now have a computer program that not only automatically gathers data on distressed properties, updates monthly (automatically), but it also gives me the mailing info I need and formatted correctly to be sent directly to the printer I use for mailings.

Once they pass the screening you can set up the lease agreement where they automatically deposit the payments into your account either wire, direct deposit, etc.

(Like, was it automatically to become a month-to-month?)

He filed for bankruptcy right before appearing in the eviction court and the eviction case is on an automatic stay.

The lease terms that I have inherited state the renewal is not automatic and must be done in writing.