@Nicholas Stevenson
Very great post with a lot of in depth questions.
I'd always recommend chatting with more reputable private/hard money lenders in your local area in order to build a relationship with them & learn as much as possible.
I have been doing private lending for about 4 years now & is a great way to be at the top of the totem pole in investments, controlling them & make the right investments on good quality deals & individuals.
Most of the others opinions were good, and you can always do it privately to learn the ropes, put your money to work, & collect the returns. Usually you can be as in depth as you want, but you should always look to improve your processes from vetting borrowers, improving lending documents, insuring that you are loaning on quality deals, not over extending, and ensuring that you are well protected in the event you may have to take it back in the case of default.
1. $250k is enough to do a deal or two, depending on the pricing of the deals & locations. If you are wanting to pool money, I'd ensure that you have done several private loans yourself to learn as much as possible then solid your borrowers. You do not want to lose OPM & you may need to guarantee them safety with additional provisions in your lending documents.
2. I'd just stick with purchases & 1st position mortgages. Usually the less you give them, the more secure your investment will be & forces the borrower to come up with their own capital & skin in the game to make it more serious. You can always do more, but I'd say should really depend on the borrower, deal & your ability to potentially collect.
3. The lower the LTV the better it is for the lender.. Your lending documents should be in depth to go over a lot of provisions in case of default & general overview of the loan. You want to ensure you get a lender's title insurance policy, ensure that the borrowers set up automatic payment/ACH draft, ensure they obtain the best insurance for the deal (i.e. if it is under renovation, ensuring their policy covers key things while the home is under construction & vacant, there are more endorsements you can get outside of a normal rent ready policy), ensure you are listed as an additionally insured on their policy, ensure they send proof of insurance + utility payments, and more...
4. I'd look to lend to investors that have been in the field for quite some time, have a lot of deals under their belt & still review them as a traditional bank would when going to get a loan or you reviewing a leasing application of a renter. You want to vet them & screen them in order to protect your money & ensure you get it back.
5. I'd just ensure you lend to stable people. Whether singles or married couples, that may have one w-2 working spouse. You can ensure to review their financials if need & portfolio to see how that looks if they are operating well. I'd avoid 2nd mortgages & renovation money, younger investors that haven't done a deal, and stick with your criteria.
You can always start off small, can also ensure any money that is idle is in a HYSA or keep reserves in a treasury bill or CD just to fight inflation. Can look at more rentals, or a house hack. I'd probably stay away from subject to & try to go with an assumable option if so. Continue to educate yourself, attend events & get in your community.