VA and Commercial Loans for MTR/STR Strategy

Hello everyone!

Newbie here. I am planning on converting my current home to a midterm rental (it's in a small town but a large hospital system nearby). I am confident it will rent well.

I need to move to Milwaukee for a few months. Instead of paying the crazy high rent prices for such a short stay, I was considering using a conventional loan to purchase a condo in the 3rd ward area and furnishing it while i lived there. When I move out, I plan to also convert that to an MTR as I understand there's a lot of med students and travel nurses in the area.

I also want to use my remaining VA loan to purchase a beach vacation home this spring/summer. I know with VA loans I have to use it as a primary residence for at least a year, but was then wanting to convert that into a STR. (Kind of house hacking? )

My questions to you all are:
1. Does this seem like a realistic plan?
2. Will getting a conventional loan now hurt my rate for a VA loan a little later this year?
3. Has anybody done anything similar and have any advice for me?

Thank you!