Making some money along the way is a bonus for him. 

I plan to do cost seg study and get bonus depreciation (and will actively participate as per IRS rules) but need to confirm if this would still work if buy STR under LLC and I can still be eligible for that STR loophole?

Offer $50 or $75 for each showing, possibly with a bonus if you rent to the prospect.

At present time you essentially have a m2m lease without the financial bonus.

If we are able to do business someday that would be a great added bonus!

Bonus question: Is it best practice to offer at the asking price, even if you discover issues with the property?

Starting RE investing in an area you know best is always an advantage than trying to invest in a state you've never been and bonus points if you learn that market and know what to expect from the investments.

So I guess anything during the offseason would be considered a bonus in this market.

(Sometimes depend on the market, I even throw in some bonus such as if they sign a lease renewal before end of the week we can get them some rent credit for the upcoming month, if the market is hot then I won't say anything) 

The bonus is if the price of the house goes up over time and you also make money from appreciation when you sell.If you hire a PM, you will bring in less money; however, you will have more time to be with your family.