WRT drilling problems the industry standard solution is make a little hole in the PCB layout so there's a ring of copper and use the stiffest sharpest carbide bits you can get but realize you can't hand old carbide the slightest side force will crack the bit, need to milling machine it.
WRT vias there is a circular problem going on with thermal vias. If you're building a shipping product with qty 10K+ and running into tight financial and thermal constraints the only way out sometimes is a field of vias perfectly flat with the silicon soldered to it and the vias dump the heat, neither air or PCB laminate are good enough thermal conductors.
So if you're building at home and want to pretend to be extremely constrained then you can manually perform the mass production steps necessary to use vias as heatsinks.
However the more rational less circular way to solve the heat problem for onesie-twosie construction projects at home is to think outside the box and bit and throw money at the problem. You can't afford a 50 cent heatsink on some consumer products but I certainly can afford fifty cents in some one-off thing I'm bodging together on my workbench at home. Or say you need squeaky clean power for a low level analog project, well, instead of crazy PCB tricks to dump all the heat in one 7805, dump some of the heat in a switcher running at 9 or so volts and have the linear reg turn noisy 8 V into clean 5V. The "CMRR" equivalent datasheet value for a boring old linear from the 70s is like 80 to 100 dB from memory so it'll be clean enough for analog work. If you try adding a $2.50 switcher to the BoM at work on a qty 100K project "to get out of needing thermal vias" your boss will have a quarter million dollar heart attack, but at home on a qty 1 project that $2.50 is like a rounding error and I just don't care. Or bodge in a beast of a heatsink if you need silence. Or bodge in a fan if you can afford the acoustic and possible electrical noise.
Now if you're trying to "Work at Home" and do a prototype, just while at home, then you have to work as if you're at work.
There are some nifty microwave ICs that as usual turn 99% of their input power into heat and they might "Need" to push all their heat thru a little grounded field of vias. Even that can be bodged using a milling machine and lathe if you make a roundish hole and plug it with a solid slug of copper. Remember labor cost at home for hobby projects is $0/hr, so something that would add ten minutes manual labor to a million product production run is perfectly acceptable at home but unthinkable at work if you can just use vias.