I highly recommend investing in a property management software, such as Hospitable, for syncing your calendar, automating messaging, and scheduling cleans, as well as a dynamic pricing tool, such as PriceLabs, for optimizing your pricing based on market demand, local events, and seasonality. 

If a policy excludes wind coverage (more common in places like Florida where insurance is severely strained by weather and other market conditions) then all wind related events are excluded.In those cases, it's sometimes possible to purchase a wind policy (usually covers wind & hail) which would provide tornado protection.

To determine what to offer on a rental property:Determine reasonable market rent, NOT the highest!

One has been rented out for four years same tenants and the other one is newly acquired and have been trying to find the best platform to market it (furnished finder, Zillow, Airbnb, etc)Would the suggestions from the real estate investors be excessive or something to look into?

I find it strange that no one has if it's allowed, but if you are first to market, you are essentially the guinea pig.

I would say you should start off by just meeting multi-family investor-friendly agents who can help get you started with 5 units search and work on finding you off-market ones as well Thanks Kerlous!

If you do not qualify, you would then look into if you would qualify with renting your departing residence. 75% of the lease will be used to offset that departing residence mortgage. as you mentioned the timing of renting the place can absolutely be tricky so you would hope you do not have to do this.Finally, and I guess would be sorta of a trick, but we do bridge loans on occasion in this case IF you can qualify once you get the property rented at market value even if debt to income ratio is too high before it is rented.

I am in the Milwaukee market. 

San Antonio is a hot market still for flipping.

I did not see marketing costs, nights that you need to spend at networking meetings paying for dinners or memberships.