Financially free always betas debt free, and taking on more "smart" debt is not only opposite of risky but actually the goal for the most seasonal investors.  

When doing them, it is best to be in and out as quickly as possible and preferrable during the storm "off-season".

He is now in rent up modeand is at 20% occupancy after 3 months during the slow season.

Sept is seasonally slow here in South FLL.

Here is some key information:Property recently hit the market and has 2 cash offers alreadyThe seller provided a pre-inspection report, which I shared with 2 different lenders, both think it may fail conventional financing due to potential structural and electrical issues (realtor thinks it could pass conventional)Seller has 100% equity but is behind on other payments (not sure of the urgency money is needed)This is my first attempt at an “investment” property so I’m new to thisI see 3 optionsMove forward with an offer using conventional loan pre-qualification-Not as attractive of an offer to the seller-Possibility that appraiser calls out structural/electrical issues that need to be fixed before closing, effectively causing financing to fail- Best terms and fewest loan fees for meUse a rehab style loan such as ChoiceRenovation-Even less attractive than a conventional offer to seller, but less risk of failed financing if appraiser calls out issues-Slightly worse fees and interest rates compared to conventional-Lenders tell me possibly up to 60-90 days closing in some cases, with red-tape for contractor requirements and draw schedules (sounds like the most hoops to jump through during rehab)Use a hard money lender-Most attractive loan option I can give to seller so I can compete-Much higher fees and interest rate for me-need to refinance into a conventional at the end of rehab (not familiar with seasoning periods but I think this is a factor as well)Which option would you do?

Seasoned investors typically have contingencies in place and work to diversify their portfolios to mitigate these risks.4.

Say I travel seasonally.

Focus on targeting investors, seasoned buyers, or those who are looking for creative financing options. 

I think it’s just a seasonal/holiday slump but it’s a good time to be a buyer!

We do a similar thing for our long-term tenatns, leases start and end in July so that we maximize the demand and stay "in season"