Yesterday, I got "good news, we removed our extra 2nd home / rental property hits, because we're so generous and nice!" 

Well worth saving that extra 20% and controlling who is actually in your property. 

To me, the extra cost and inconvenience of separate closings is worth it!. 

It will be cheaper for the company - and I will take extra profit and not a random landlord or hotel owner.It's important to say that I already own a house which I am living in.Now here are the questions part:What is the really best way to do it tax-wise?

I also wanted to add 2 storage sheds so that each unit has a shed they can store extra things inMy thoughts were that if we are adding features to the units/upgrades, does that mean we can charge higher rent (I was thinking $1350-$1500). 

Took extra attention when writing my lease agreement and reviewing applications to find renters that behave like homeowners (require them to mow their own lawn to avoid lawn care expenses, all utilities except for sewer/trash are tenant responsibility) which has paid dividends in reducing headaches and keeping time spent on management to a minimum.

He can probably get discounts on materials and how much extra time would it involve for both of you if he needs you to get the materials every time and if you get the wrong stuff.

Looking at local listings I think I will be able to net 500-800 extra per month.

However I recommend investing in college towns as student rentals are one of the best ways to extra higher rent.

I treat them well, as far as soon as they finish the job, I pay them via an app, and they seem to really appreciate that and go the extra mile when I need that.