Introduction and question....
You'll definitely want either an Arlen Ness Big Sucker or a KN set up. A lot of people prefer the PCIII or SERT to the V&H but on my salary, I had to go with a Fuelpak I found on this site for about 100$ used. Works well enough for me. And yeah I don't see myself doing a Stage 2 set up for a long time just because of how pricey that can get.
First, a big Thank You from my family and myself for your service to this great country.
IMHO, it's OK to let the bike sit for a week or two without doing anything to it. Parking on the carpet or on a tarp(vapor barrier) is a excellent idea.
If you trust him riding it, as it sounds like you do. Instead of just letting it run for 5 or 10 minutes, then shutting it off, have him take it for a short spin 5 or 10 miles would be much better for the bike. Just starting it and letting it run for a few minutes can do more harm than good. A lot of acids and moisture can accumulatein the engine, and by not actually riding it they can build up and shorten the life of the engine. Sounds strange, but it's true.
You made an excellent choice with the Street Bob,if you ask me. But I may be a little biased

Stay Safe and hurry home to enjoy the Harley life with us.



