Norfolk,Portsmouth,And Suffolk are areas I am researching extensively and i am very interested in learning more about .

Do you have extensive construction experience?

At that time, offer a full lease extension (might even be able to push the rent up a bit, but I'd focus primarily on getting yourself back on-season and then get a lengthier/standard 1-year lease signed.

Termination 'fees' are generally limited to what you have in hand...especially without proof of extensive property damage done by the tenant forcing you to keep the property off the market while you spend time and money to make it market ready. 

I’m currently looking at a house as a live-in flip while renting the lower level (with my back up plan being a regular flip or multi rental).It’s listed for $365k but my offer will be closer to $210k due to the extensive repairs.

If you agree buying for yourself is not an issue, then your employee (buying for your account) is a direct extension of you.

We already had to pay extension fees on the hard money loans because the loans had gone past their original maturity dates.  

Unmitigated water damage becomes mold damage and and there is the potential of extensive smoke damage in the same airspace.

As many guests do, I also assemble and update a guidebook of local recommendations that rotate by season (since we have 4 where I live).

 Some won't do newbies some will.Don't pay any funds upfront other than appraisal, watch out for points those get expensive, being your new ask what it cost for extensions.