Field Service Advice (FSA) Memorandum 2001-37003 states that the two-year holding period is prioritized over Section 1031(f)(4) if you adhere to the time frame.

Any advice would be vastly appreciated, and once I am finally in Vegas, I hope to continue to build connections and collaborate with whoever I can.

This is super helpful, and I appreciate you mentioning what I should be thinking about and prioritizing during my process of looking at CRMs! 

I am new here and already loving the collaboration.

I'm new(ish) to the mid-term rental space and would love to collaborate with people in the area who are using this strategy.

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

By collaborating, I hope to explore future investment opportunities together.

Collaborate with trustworthy: Engage reputable real estate agents, lawyers, and appraisers who have a solid track record and are licensed or certified.2.)

Prioritizing at least a positive cash flow for our first investment property, if at all possible 

This includes ensuring you're accurately tracking all eligible expenses, maximizing depreciation deductions, and planning any potential 1031 exchange if you decide to sell and reinvest in another property.In all cases, the key to a successful investment strategy is careful planning, accurate record-keeping, and collaboration with professionals who have expertise in real estate, tax, and legal matters.