I would have to say after next years tax season would be the best time!

Here is an older discussion on this topic that you may find very helpful:https://www.biggerpockets.com/forums/51/topics/527...And if you search the forum you will find many more...

As a seasoned real estate investor does this sound like insanity?

I have been involved in the past about sales managing and maintaining commercial properties as well as construction projects into retail, banking, movie theaters, and a hotel.For about a year I have been watching and listening to a gentleman that has about 25 years in the experiencing of successful real estate buying and selling apartment complexes and currently owns almost 5,000 apartment units. 

I do not invest in them but have clients that own many.Running a high end flag hotel is much different than an older building dive type place.

And while I've heard most banks require at least 1 year of seasoning, I've also seen local banks refinancing in as little as 6 months.

I asked, but the gentleman who was working was not giving me a straight answer and the connection was terrible.

I'm unsure if they do business with new investors vs. seasoned ones, but I had a great experience and would recommend them.

My Lake house does better, but is seasonal (late spring to early fall) and Clemson home games and I am around 60% vacancy rate. 

. $85-90/sq ft homes are about what my area is going for but older homes with larger lots.