Andries,
Congratulations on getting started on your REI journey! I am also a N. Virginia based investor who owns properties in the Hampton Roads area.
To your question of is now the right time to enter the market? I would say it really depends on what you are trying to do? Buy and hold, fix and flip, BRRRR, etc... I believe there are strategies and deals to be had for every market cycle, maybe it just might take more time to find them.
I find it is useful to talk to many people involved in REI in your area to get their opinions (and property managers are definitely a great source), but at the same time you need to formulate your own ones based off your own research. Have a look at the data related to vacancy, rents, collections in the Hampton Roads area, by in large the area has performed well. For my properties we have maintained 95+% occupancy and collection.
In terms of looking at mortgage forbearance going away, I would recommend looking at and underwriting deals where you are not factoring this into your strategy. While the forbearance may be being offered, it could make it harder down the line to secure loans as you look to grow your portfolio.
While these are certainly more uncertain times than normal, I still believe you can successfully underwrite deals. Something to think about; how big of a factor will a potential end to renter assistance be? If your property is in an area that rents heavily to govt/military (like some areas of Hampton Roads), then this may not be as big of a factor as these jobs are likely more secure. If it is a factor, and say for example much of the tenant base is in the service industry, then have this discussion with the seller and ensure the risk is reflected in your purchase price. Keep in mind the concerns you have buying, the seller likely also has in holding so may be more willing to negotiate on price.
Wish you all the best in your search, feel free to reach out or direct message me if you ever want to discuss REI more.