Shifts hard at first (when tranny is cold) then seems to shift fine. Checked tranny fluid level and it was low by a few quarts. Could this have been the problem or am I in danger?

This may have been problem[low on fluid] may be time to change that trannny fluid and filter. if you choose to do this , i recommend that you add lucas tranny treatment to the fluid change also w/new tranny filter. this frees up any sticky valves in your tranny. allows smooth shifting, and works well wlth any fluid for fords/chevy's or jeeps. the lucas will eliminate the hard shifting, been there done that issue. also the hard down shifting you did'nt mention. although you may have not noticed. add the lucas and your hard shifting issues should be gone. thank you for choosing fixya.com

It acts like it doesnt want to go in gear but it will after a little bet

Your transmission holds about ten quarts of fluid...However, the last quart and a half are the most critical as without them the filter ca pull in air that can easily cause internal clutch and seal damage.
How much damage is impossible to know without actually taking the unit apart.
I do recommend that you locate the reason the trans was low, and stop that leak. It's also a good idea to add lucas trans sealer and conditioner...it may help mitigate any damage and if it's not too bad you may get more use out of it.