Bulldozed the house and plan to build a new house on lot in the future Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Although I do plan on increasing the rate next year and so on and so forth.

My plan is to rent it on a short term rental basis and stay for few weeks in a year with family/friends. 

If you move title to the property into a trust for the seller's "Estate Planning purposes", you still need the mortgage company's approval. 

I have a degree in civil engineering and 15 years construction, site development, and short term rental experience and am looking to shift my focus/career towards real estate development, mainly raw land although if there were a house on the property could include fix and flip.I plan to purchase 50+ acres of raw land with 1000+ feet of road frontage, have it surveyed and split into separate 5+ acre parcels for re-listing.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

In other words held for steady cash flow.My VARIABLE (note) PORTFOLIO consists of more active/speculative notes - non performing notes I purchased at discount to principal owed; notes I hope to “work” for enhanced ROI, real property I “purchased” with a leaseback option to repurchase, and defaulted notes I purchased planning on eventually taking ownership of the real estate, as well as notes I created that don’t have current payments but provide a guaranteed return plus an equity “kicker” when the property is sold. 

One thing to note is that I wouldn't plan for appreciation.

There are many ways to house, and even more way to plan for the future with 1031 exchange and Primary Residence strategies!

My goal is to achieve financial freedom by age 36 and to understand various aspects such as investing education, strategies, business planning, properties, marketing, and exit strategies.