Can you really raise the rents and keep the tenants or will they bounce at the increase?

The goal in my implementation is to minimize the bounce rate when filling the funnel, so I like your 'flow' on the main screen of View current property -> Schedule a showing -> Application... which may answer question #2 above (Also, send me a PM with your email if you want spelling comments offline...)

I hope to bounce some deal analysis off of some weathered investors and to understand the business and legal aspects of real investing.

I'm just bouncing ideas around in my head now.

When those regulations later got rescinded, the price bounced a little up but since has continued a slow decline. 

It doesn't make sense that they would try to bounce it now when you had it on there the whole time.

I'd like to sanity-bounce them off someone and make sure they are in-range.

The income will not bounce back on these assets quickly.  

I want to get started, but I would really appreciate having like-minded individuals with real estate experience in my corner; having even one person to bounce ideas off of and point me in the right direction from time to time would be hugely beneficial to me and my real estate career. 

One assumes they'll bounce back but time will tell.