Or what about the syndicator who wanted to complete a condo conversion but the units are going to be geared towards empty nesters and that buyer is not motivated to make that next move until rates calm down & the GP is forced to continue to carry a building as a rental asset when that's not its true or highest and best use but still projects to be an excellent development once the market conditions are better aligned..... 

It's crucial to align this decision with the nature of your income sources and their respective tax treatments.

Make a list of all assets and their components (how many roofs, refrigerators, heating systems, etc?)

Your decision should align with your overall investment strategy.Consultation with Real Estate Professionals: It might be beneficial to consult with a real estate agent or a financial advisor familiar with the Windsor market.

Plus, it's one of the key components to a successful STR! 

My flexible budget for each property sits at around $150k.I'm eager to connect with experienced investors and gain valuable insights into potential markets that align with my financial goals.

It's important to consult with a tax professional who can advise on how these strategies align with your overall financial situation, especially considering your full-time employment and income structure.Moreover, as your portfolio grows, and particularly if one spouse can transition away from W2 employment, the landscape of your income and tax liabilities shifts.

Very much like the moon and stars need to be in perfect alignment, but it does happen from time to time. 

Maybe determine a cash-on-cash figure that aligns with your comfort level.

It's a budget friendly option to some of the other services, and they have engineers on staff + audit defense, but the more expensive cost seg companies ($1500-2500) will actually do walkthroughs of your property via Facetime to more granularly estimate components of your structure.