First of all, sorry to hear about the difficulties. I've been down that road and it's not fun.
I'm going to have to keep this short, cuzz, speaking of kids, I got three of 'em that need to be driven all over the place. But let me make a few comments:
--Imo there is no practical difference between 210 and 290. I would be very surprised if you will feel any improvement in symptoms. 290 is just a hair breath above what most labs would consider hypogonadal (280) and the lower end of those lab ranges are abysmally low imo.
--I understand about your concerns about the possible long term effects of HRT. So far science has not found any long term effects as far as I know, but none of us has a crystal ball and so perhaps some subpopulations will be at risk in certain cases. Who knows?
--I think you are wise to go off the topicals if you can. That's my personal opinion. Supposedly, according to one study, transferrence is not a concern. I am skeptical however and think it's important to play it safe. In the case of small children, this has the potential to be brain-altering, and I have kids and would never want that on my conscience. Realize, though, that there are many alternatives that are safe imo: injections, Axiron, patches, pellets and possibly Forestra.
--If you there is any chance you want to have kids, then HRT is not a good idea, again imo. The great majority of men will experience decreased fertility. Use the search on my site and this forum regarding to look up things like Clomid, Arimidex, etc. And I've got imho one of the most int'g pages on fertility as well:http://www.peaktestosterone.com/Improving_Fertility
--You must balance your concerns about testosterone therapy with concerns about NOT treating testosterone. And in your case when I say "testosterone therapy" I am including Clomid/Arimidex btw. PM me and I will send you my book on testosterone. In this book I document all the increased risks of being at low testosterone (less than about 350 or 400 ng/dl): diabetes, venous leakage, Metabolic Syndrome, osteoporosis, erectile dysfunction, depression and on and on. Again, I'm not a doc and can't tell you whether or not to go on pharmaceuticals or HRT, but you should be fully informed before you make a decision.
--As you know, I am a huge proponent of a natural lifestyle. However, I have not seen much success with boosting low testosterone when a man is hypogonadal like yourself. The exception is with a large amount of weight loss. But, of course, you have little to nothing to lose! So I encourage you to read through my site and try to improve your testosterone through lifestyle means, such as increasing sleep, improving your mental attitude, increasing Vitamin D levels, making sure you are getting adequate base nutrients, etc. However, my experience is that men generally are not going to go from the 200's into the 500-1000 range from lifestyle alone, which is where someone your age would normally be.
--Last thing. Here is some good starter info on testing to discuss with your doc:http://www.peaktestosterone.com/testosterone_tests