I have only 3 doors that I manage so not a big time player so wanted to start with some cheaper software and I heard on the podcasts that RentRedi was included in my pro membership so I signed up.  

Most DSCR loans will have very limited seasoning requirements to use the new appraised value to refi.

I am assuming you know about this, but you may want to consider doing something like a Wally Wrap so that you have an asset to show your next lender prior to your note seasoning.

We host a free real estate meetup the first saturday of every month if you are interested in coming and meet some awesome real estate investors who are looking to do their first deal to savy seasoned investors.

I've stuck with the tried and true reasons I've heard to keep my search ranking high (quality photos, stellar reviews, updates to my listing) and that helps but in slow season, when I'm not willing to cut my rates as much as some of my competitors, it can be a ghost town.  

If you don't meet that 12 month seasoning requirement and/or want to hold the property under an LLC, a debt service loan may be a better option.

What’s your occupancy rate during peak and off-peak seasons?

Then after the units are stabilized (perhaps with some seasoning), you could get a bank/HML to refi this up for 75%-80% of the ARV.  

As a senior baseball player looking to eventually play pro ball after this spring semester, I acquired a serious interest in doing real estate as another source of income.

When it starts to rain in monsoon season, put your galoshes on. ;-)