Lets start with your second question first.

IFR currency requirements are found in 14 CFR Part 61.57(c). Once you receive your instrument rating (and the approaches you do the day of your checkride count toward currency), you must within the preceding six months in flight in the appropriate category of aircraft (in this case an airplane), or in a flight simulator or flight training device that is representative of the aircraft category (again, in this case an airplane), complete at least six instrument approaches, holding procedures, and intercepting and tracking courses through the use of navigation systems.

So to stay current you must shoot six approaches every six months in actual or simulated conditions (sim or in flight with the hood on). In addition, do a hold. Because you must intercept and track courses using navigation systems to do all that, you're covered. Actual conditions means in wx conditions less than VFR mins for the airspace you are in. So let's say you are shooting an approach in a class D or E terminal area. That would mean the wx must be less than 1000' ceiling and three miles. If it's not, you can't count it. There is a current push in the FAA to not count any approach that doesn't go to minimums. However, most will accept any approach in less than VFR mins.

To regain your currency should the six months lapse is still fairly easy. If you are not current, you have an additional six months to get current. You can not fly in conditions less than VFR mins until you are current again, but you can have another pilot act as a safety pilot while you shoot whatever additional approaches you need to meet the requirement of six, and do a hold, in VFR conditions with the hood on. If you still don't get them done within the additional six months (we are now past one year), you will need to get an instrument proficiency check (14 CFR 61.57(d)).

That said, this is the bare minimum. I do not recommend staying current only to this level. If you are really going to use the instrument rating, I highly recommend you fly every six months with a CFII and obtain a proficiency check, with as much of the flight in actual conditions as possible. Treat it the same way we do in the airlines. Require of yourself "recurrent" instrument training every six months. The additional cost of the instructor is just not that much.

First question. The reason your instructor is suggesting you get the additional 14 hours of XC first is two fold: one, he wants you to get more experience in the VFR environment, navigating, pilotage, dead reckoning, tracking courses. This will build your experience/confidence and begin to "wean" you from his support. Second, he is trying to save you money. By not having him in the cockpit, you aren't paying for him.

You will do about 15 hours of XC during your instrument training. So he has that about right. My suggestion is sit down with him and plan several XC flights that set some specific instructional goals. Review your flight plans with him and then...go fly! Enjoy it while you can.