Here are my thoughts, if HDB continue to fall, good.
Since your budget allows only old rundown FH VS a new LH Condo, you need to know your needs. Frankly, I know the temptation to get newer LH condo is there but I would not touch, as it is short term benefit by long term pain, if you want to sell a depleting lease property later for whatever reasons.
An exception to me buying a LH condo is those with Mall / MRT below, ie, mixed development type, these LH condos hold their value well.
OK if all else out of reach, do consider less than 10 year old HDBs in prime areas near the city, or next to malls / MRT to me, if you can get a good deal, they are very good value for investment or own stay and cheap and easy to maintain.
As for big open balconies, I love them especially on high floor with good views, you can put a nice two piece dining set and relax with a beautiful skyline view. At least in Singapore, city views are the only real views, we do not have real sea views, river views or lake views, no matter how glossy the brochures look. I like City View DBSS at Boon Keng in particular.
Forgot to say that buying two smaller properties do take into account ABSD which may be quite sizable, especially so in proportion to smaller quantum purchases, so may not be worthwhile, that is why l started buying overseas now.