It sounds like you want to make all preparations up front, debating this and that, as an excuse to avoid actually doing anything. How much do you know about electronics? Pick a project and build it! You don't require anything but a computer to design a pcb. See here for free software:
http://www.4pcb.com/ They also make your board in low runs for cheap prices. My impression is that you haven't yet conceived of the available opportunities. IoT is probably the most wide open field in electronics today. It involves using the Internet to communicate with and control other devices and systems via smart phone or computer, or between two different IoT devices.
But for starters, you probably do fine with a 3-1/2 digit multimeter for under 20.00USD. You can get a 30V 5A DC variable PSU for about 30.00USD. A 20 Mhz dual-trace USB DSO costs about 60.00USD. You can get a good laptop for 200.00USD that will run anything you want.
I picked up an USB EEPROM reader/writer for 40.00USD. It works with many chips, even old ones. I picked up a DMM on DHGATE for 80.00USD that does vdc/vac, resistance, Idc/Iac, uA, mA, frequency, period, cap, diode, temp, RH, luminosity, and SPL.
Interconnects (think pomona), bread board stuff, assortment of board-level components, soldering station, tips, tinning compound, solder, flux, copper braid, solder sucker, heat gun, shrink tubing, jump wire, hand tools, and connectors will run another few hundred. Get a decent soldering station. I recommend a basic Weller unit.
You'll also need a cordless drill, rotary tool (think dremel) a mill and some end mills (drill press with a vise works in a pinch!). I never tried to buy everything I might need. I used the same soldering iron and tip for 10 years. You get to know the stuff you have and how to get the most out of it.
But before you make the jump, pick some project, and get just what you need for that project. When you complete the project, if you still enjoy electronics, pick a bigger project.