I would definitely hire a management company if I plan to rent the property.Back up plan is to stay there two years, sell the property and avoid paying taxes.Fellow BiggerPockets community, I would love some advice on evaluating whether I should flip the property to reinvest in a bigger home or multifamily unit or rent the property with a management company?

I've been targeting the Vail Racquet Club ever since my stay there during the Vail Alpine Ski Championships in 2014.

I often take massive road trips and will stay at a mix of STRs and hotels or quirky lodges depending on what looks fun or convenient. 

Any stay over 30 days is considered Mid-term and may not have the same restrictions a STR would.

Quote from @Phil Chehet: Hi , looking for a Subject To friendly Title Company to process deals for us in Toledo Ohio area Bruhhhhh stay away from Sub2.

I am really excited to have discovered this community and be able to gain insight and knowledge from all of you! 

My best advice is to find someone who is doing what you want to do, and then offer to bring value to them (for "free") in return for mentorship, guidance, and knowledge. 

It is my opinion that you should stay far away from them.

Also depends if you plan to sell those and move to bigger rentals of if you plan on staying with 2-4 doors. 

If the plan is to stay with a commercial loan, the construction finance and permanent loan can be one product, with typically a 12 month interest only period during construction, then rolling into a principle and interest payment afterwards.