Find out what your market is like in Sept (guessing quieter than the summer) and see if you can get the tenants to move out sooner. 

Then, the sooner the better.

Generally, you can get someone out in 45ish days on the long side, often sooner. 

The sooner you start, the sooner you will feel more comfortable with the idea of investing in a property. 

No sooner had I thought that and boom!...

Having a good partner with good communication will be key if you want to get started sooner than later.  

Olympic sized pool, hot tubs, on-site restaurant, yoga, pilates, gym, steam, sauna, and management company to take care of it all.

The two most obvious options at hand are : A/ Accumulating capital through my job before investing in real estate B/ Asking for a bank loan that would allow me to invest sooner, saving time, after doing market research Which strategy is better, in your regards ?

The life of a DST is 7-10 years, some go full cycle sooner.

Get the next place sooner, you're still cash flowing and you're not putting more money into the deal your already in.