Also, just to confirm, for it to turn over, I will need to have the tractor in neutral, brake pressed or parking brake on and PTO off.
No. ....Your Bolens 1000 was not equipped with the safety interlocks which were added on later tractors.
HOWEVER, for safety and to lessen the load on the engine when trying to start it, the PTO should be "OFF", and you should press down on the clutch. ....Having the transmission in neutral is just another way to prevent the tractor from moving when it is not wanted.
If your 1000 is wired correctly as it was originally equipped, pushing the starter button will crank the engine. ....It will not start unless the key is "ON."
I apologize if I am not giving enough information, I am just trying to get my head around what I need to get this working. I know I am missing the push button start, need a replacement switch and may need a new voltage regulator or solenoid. Would it be easier to just start fresh with a new replacement solenoid/voltage regulator/push button/switch combo?
You have 2 choices: Either make it like it was originally, or make it like some later models were.
If you use the large "Heavy-Duty" pushbutton starting switch, you do not need a solenoid.
If you use a small (light-duty) pushbutton switch, you will need a solenoid.
If you use an ignition switch with the "off-on-start " positions, you will need a solenoid. .....This style switch will have 12volts coming to it, and 12v going to a solenoid in the "start" position. .....This style of switch is used with a round-can ignition coil, and is not suitable for magneto ignition unless it isolates the ignition circuit from battery voltage.
The original "off-on" key switch did not use a solenoid. ....It was not connected to battery voltage!!!
Another suggestion: Work on one part of the wiring circuit at a time to avoid confusion.
The voltage regulator has nothing to do with the cranking or starting of the engine.
The solenoid and/or push-button has nothing to do with charging the battery.
Your engine would never utilize a round-can coil and a magneto, so you have to decide which system you want to go with.
Keep in mind that you also need a correct-style solenoid, if you choose to go that route.