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" 

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

And you suffer during the off season right?

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

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

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?

Your income needs to be 100x it and you need to invest 10% of your net(so less than $5mil) annually in structured product type investing incl RE, let it season for 3-5 years, re-invest the first bit of profits and by year 8-10 you should be comfortable.$500k annual income is alot for your average folk, but it's not "retire me" income at all.

Nobody likes to work hard in the heat.The biggest concern in the past has been winter, but 2024 was the warmest year on record and we have seen +3F on average in every season, which really took the edge of winter (you can call it brown grass season now) while summers are pleasant 75-85F.The cost of living is low, yet the quality of live is relatively high.

The market does pick up in the spring, due to seasonality, but the 10yr yield will be more indicative of buyer interest.

Would love feedback and learn from the seasoned professionals.