You can see that talk of "flying for free" doesn't go over well so best not mention it in a forum of pilots looking for jobs.
In the current environment, very few are getting called without recent turbine experience. There are a few...but they are like finding a unicorn. Much of it depends on the total strength of your resume/experience and each company is different. In 2 years the hiring environment will be different and companies may be entertaining larger gaps in experience for military trained pilots. I don't know how much will change, but I'm starting to think that in the 2020-2021 timeframe the majority of new hires at the majors will be Mil Helicopter Pilots after their 2-4 years regional experience.
Here is my personal opinion - focus on your command assignment. Give your off time to your family/friends/hobbies. The transition prep will take a huge chunk of your time away from work even without dividing it between a "2nd job". The transition is almost a full time job! Submit your applications 1-2 years out from your terminal leave date. This would have your applications hitting the street with maybe 1 year out of the cockpit - thats not too bad. Shotgun the apps to all the majors (typical military approach) and plan on going to the regionals. If you get called by a major...great...if not...execute the regional airline plan but don't expect to stay there for longer than 12-24 months. Recent rumor is that AA gave a CJO to a mil pilot that was 18 months away from their separation date.
In general here is what seems to be considered "current":
UAL - 100hrs in something more complex than a 172.
AA - 300 hours according to recent webinar
DAL - 200 hours of turbine
FedEx - 200 hours turbine
UPS - Unknown
This "non-current" mil pilot issue is an emotional and controversial topic. It clearly has nothing to do with ability but more so on PERCEIVED risk to the company and pilot. The perception is that there is risk of additional cost to the company to train a non-current mil pilot as well as the career risk to the mil pilot if they fail a 121 training program with a major airline. This is PERCEPTION and not necessarily reality but business is business and decisions are routinely made on perceived risk. The REALITY is that airlines and the military routinely train folks that have been out of the cockpit for years. Anyway - accept the facts of the business and move on.