@Mary Jay
I think you have a lot of great replies to your questions presented. You seem to have some very high expectations and they will be very difficult to achieve in the period of time you are looking at.
I don't want to tell you that it is impossible because it can be done and has been done by some. I think I explained to you in a previous email that I was lucky enough to be in the right place at the right time and was able to go from zero to retired in seven years. This is covered and outlined in a book I wrote years ago. I want to repeat, I was lucky and I worked day and night and had some other benefits as I have mentioned before. Obtaining my real estate license and then a broker's license in California and Colorado definitely sped up the process As well as serving as general partner for many syndications.
Here are some thoughts I had in answer to your questions and also in regards to other replies you have already received.
Does your son have a job and help with his financial planning? If not, I feel you are leaning too hard on being an enabler, which is never good in my opinion. Is he going to be contributing to the automobile and his college financing? I believe a community college is a great way to start and I used that partially in my early days.
You need to work on a very poor trait that you currently admitted to having. If you are not very good at saving money, you will never achieve the goals that you are expecting, in my opinion.
I have never felt that Cheap houses are really cheap. The appreciation is next to nothing, the depreciation is very little due to the value being in the land, and the expenses for management and maintenance are always high. I also personally prefer to stay completely away from condominiums as they are never truly free and clear due to special assessments that are always lurking on the horizon. I have always practiced what I preach. Owning over 1000 single-family residences In my lifetime, I can only remember two condominiums.
The suggestion to purchase a four Plex and live in one of the units using FHA financing was a good one. The first property I ever purchased was a duplex in La Habra California On an FHA 221D-2 program and it later became my first fixer-upper and my first property exchanged! Great story and is somewhere here on bigger pockets as well as related in my book.
It was much easier to assume loans in the old days and there was no limitation on how many loans you could finance. I would assume you have done your homework to verify that you have the ability to qualify for more than one additional property. It seems to be much more doable when you are occupying all or part of the property as the owner.
You have received some great replies to your original email and I have voted for several of them. My two favorite ones were from Shiloh Lundahl and Steve Vaughn!
I wouldn't vote for any one of your three options but rather try to use a part of each one. It will be much easier to try and obtain financing while you are still working. A combination of single-family residences and multi-units is what most successful real estate investors have done. It seems to come naturally. The movement from single-family to small multi family to large multi family is the path that I took.
There are also additional opportunities you may desire to use to help the process. Many posters on bigger pockets have gone the route of starting their own management firm to share the expense and also build speculatively or your own home. Tax benefits can be enormous in your estate planning. One of those is to have the flexibility of moving every two years and having a capital gain free and clear.
Good luck and I would reread all the replies you have received. There are some excellent points you have been given.