Tough to say

I have tried the (collection of) ramshackle "bargain" bikes and whilst you can do it cheaply it has the drawbacks you mention plus the time cost of constant, often relatively major repairs.
On the other hand if you go for new or nearly new you are often tied to getting it dealer serviced, in my case the dealer went right downhill and then combined with a well known local rip-off dealer

so then you choose between no warranty/reduced resale/trade in value or being ripped off every 4,000 miles!
The third way (shudder), is to buy a younger used bike... say two to three years old low mileage and clean... but you'd better be very confident about your luck and judgement because there are a lot of lemons out there which look very very nice with buyers eyes on!

My current train of thought is that it is probably best to buy the type of bike carefully (big thumpers are untrendy enough to be a good choice!) eg, price has levelled off (at about £900 to £1200 for decent useable big thumpers just now I think), they are obviously used without being festering heaps of corrosion (he says looking sadly out of his window

) and they are low to moderate miles.
I would use as an example a DR650 or similar, looking for pretty standard (save for things like crashbars, handguards, scottloiler etc etc) clean, around 15 to 20K miles with T&T and life in the tyres, chain, brakes etc. Smaller (eg 350) could be nice but the bigger ones are less likely to have been thrashed. Use it until 1. someone offers you what you paid for it or 2. it looks like it may be going to break something major or 3. you start wearing out not the bearings but the spindles etc, or hit more than 60,000 to 100,000 miles. (your choice).
Then sell it for whatever it'll get and buy something similar.
The workhorse 500 twins look particularly good choices for this, a few years ago I'd have said GT500/750 Kawasaki but they're too old now, if you want reliability (and for this you do) then buy somthing that is still made or stopped in the last few years. Spares for semi-moderns can be a pita!
Anyway, the scotch is rambling now (hic) so I'll shut up and go back to my housework
