What strategies do you utilize for those folks who can't use a computer to apply online? 

Best online study and license prep sites.2.

It would be a vanity play, stoking our egos to move into a nicer house. 

I have another home coming on line next month that will have an outdoor kitchen, pool, putting green and sleep 15. 

If your portfolio is a good deal you won't have an issue finding buyers.If you truly have control of a package is one thing, if you are trying to play match maker with no real control, that is a weaker position.

Our game will have to play out where we are both onboard.

Something that also does online applications and credit checks etc?

@Derek A GriffinInvesting an IRA into real estate is purely a diversification play. 

• What are the average rents for the area (there are several online tools that can help you out with this)• What are the schools like in the area• Is the area primarily SFH, Multi-family or commercial? 

Start a document that outlines every system in a home and start compiling pricing information based on information from contractors (I used to be a GC and I'd rather give someone a price per SF over the phone rather than visit the property thinking they're ready to work), information from other investors, asking questions online, friends and family that have had work completed on their homes.