@Michael Sheibar Lets first start with the type of policy you are purchasing. While it is being rented out for a week at a time you will be able to use a short term rental policy which is a "residential" type policy. Depending on who your personal carrier is you could potentially get this policy through them and then a 3-5mil "residential" umbrella would cover your autos, home, camper, boat, atv and your "residential" rental properties up to a certain number. For rentals most carriers will still extend umbrella coverage even if you have them titled in an LLC.
When it comes to umbrella pricing the carrier wants to see that you first maxed out the liability on the individual asset policy. This will help with the umbrellas pricings as the chance of using it is now much lower.
Now one item I cannot speak on is the student housing policy my carriers do now offer it and I almost never run into it so I have little to no experience with that coverage. I can tell you all my carriers will say no, unless the student is in a graduate program.
Now back to normal long term or short term non student rentals. If you own several properties and decide to buy a "commercial" insurance package you have now changed the game and the type of umbrella you will need to buy. The houses can be titled in either you personal name or your LLC but because you went to a "commercial" policy your umbrella coverage will also have to be a "commercial" policy.
You will be able to buy a supporting umbrella policy no matter what policy you have and no matter how you have it titled. Insurance carriers love to sell umbrellas and will never not offer it no matter the industry, the policy, the risk, the asset, I mean hell insurance companies take out policies on each other now to mitigate major storm losses.